bluuebunny/crossref_metadata_2025 huggingface dataset:
Kinetic Study of the Oxidation of Catechols in the Presence of Some Aza‐crown Ethers by Digital Simulation of Cyclic Voltammograms
Authors: Nematollahi Davood , Mohammadi‐Behzad Leila , Davarani Saied Saeed Hossainy
Published: March 2009

The electrochemical oxidation of catechols (1) have been studied in the presence of diaza‐18‐crown‐6 (DA18C6) (3a), diaza‐15‐crown‐5 (DA15C5) (3b), and aza‐15‐crown‐5 (A15C5) (3c) as nucleophiles in aqueous solution, by means of cyclic voltammetry and controlled‐potential coulometry. The results indicate the participation of electrochemically generated o‐benzoquinones (2) in Michael‐type reaction with aza‐crown ethers (3) to form the corresponding new o‐benzoquinone‐aza‐crown ether adducts (5). Based on ECE mechanism, the observed homogeneous rate constants (kobs) of the reaction of o‐bezoquinones (2) with aza‐crown ethers (3) were estimated by comparing the experimental cyclic voltammograms with the digital simulated results. The calculated observed homogeneous rate constants (kobs) was found to vary in the order DA18C6>DA15C5>A15C5.
Sensitive and Selective Electrochemical Analysis of Methyl‐parathion (MPT) and 4‐Nitrophenol (PNP) by a New Type p‐NiTSPc/p‐PPD Coated Carbon Fiber Microelectrode (CFME)
Authors: Tapsoba I. , Bourhis S. , Feng T. , Pontié M.
Published: March 2009

A novel modified carbon fiber microelectrode (CFME) was obtained by combination of tetrasulfonated nickel phtalocyanine (p‐NiTSPc) electroformed film associated to para‐phenylenediamine (p‐PPD) electropolymerized outer‐coating. The modified CFMEs where denoted C/p‐NiTSPc and C/p‐NiTSPc/p‐PPD, respectively. These electrodes are dedicated to the organophosphates compounds (OPs) methyl‐parathion (MPT) and para‐nitrophenol (PNP). Our contribution shows that both OPs can be determined simultaneously on the unmodified and modified C/p‐NiTSPc CFMEs. A clear electrocatalytic activity towards both MPT and PNP redox process was observed, for the first time, in presence of p‐NiTSPc. The obtained sensitivity for the C/p‐NiTSPc CFME was 80 nA L mg−1 in the concentration range 0.01 to 10 mg/L with a detection limit of 40 μg/L. Also the combination of p‐NiTSPc and p‐PPD electrodeposited films show, for the first time, the possibility to discriminate on the C/p‐NiTSPc/p‐PPD CFME between MPT and PNP. Stability experiments were also conducted for 3 weeks in acetate buffer showing a good reproductibility of the sensitivity to PNP vs. time in presence of MPT with a little loss of sensitivity (5%) after 3 weeks.
Microchip frontal affinity chromatography to study the binding of a ligand to teicoplanin‐derivatized microbeads
Authors: Liu Xiaojun , Gomez Frank A.
Published: March 2009

Microchip frontal affinity chromatography was demonstrated to estimate the binding of 5‐carboxyfluorescin‐(D‐Ala)3 (1) to magnetic microbeads derivatized with teicoplanin (Teic) from Actinoplanes teicomyceticus. In this technique, a cross‐chip was used whereby the two side channels contained an identical length (1.5 mm) of derivatized Teic microbeads (affinity column) and underivatized beads (control column), respectively. Cylindrical NdFeB magnets were fabricated into the PDMS chips to retain the magnetic beads. Upon application of a voltage, a sample of 1 was continuously introduced into the affinity column followed by a buffer wash and the same sample from the control channel. The extent of interaction between 1 and the two types of beads in either microchannel resulted in differences in migration time of the ligand as detected by fluorescence. This difference was used to obtain a value for the binding constant between 1 and Teic‐beads of 5.4×104 M−1. This technique reduces the amount of sample needed for the binding assay as compared with conventional frontal affinity chromatography techniques.
Enantioselective in‐line and off‐line CE methods for the kinetic study on cimetidine and its chiral metabolites with reference to flavin‐containing monooxygenase genetic isoforms
Authors: Hai Xin , Adams Erwin , Hoogmartens Jos , Van Schepdael Ann
Published: March 2009

An in‐line screening and an off‐line chiral CE method were developed to determine the stereoselectivity of flavin‐containing monooxygenase (FMO) isoforms using cimetidine (CIM) as a substrate. The S‐oxygenation of CIM was investigated using achiral chemical oxidants and (human supersomes) enzymatic metabolism procedures. In the off‐line setup, the chiral selector sulfobutylether‐β‐CD was chosen to separate the CIM S‐oxide (CSO) metabolites. The electrophoretic migration order of CSO was confirmed to be (+) before (−) through the use of single enantiomers obtained by preparative chromatography. For the electrophoretically mediated microanalysis method, the in‐line enzymatic reaction was performed in 100 mM phosphate reaction buffer (pH 8.3), whereas 50 mM phosphate buffer with 30 mM chiral selector (pH 2.5) was used as a BGE. During the screening of FMO isoenzymes by the electrophoretically mediated microanalysis method, formation of the new chiral center on the CIM sulfur was found to be stereoselective. FMO1 produces more (−)‐CSO‐enantiomer, while FMO3 generates mainly (+)‐CSO‐enantiomer. On the other hand, FMO5 shows no activity. The kinetic constants of FMO1 and FMO3 were measured by the off‐line method. AKm=4.31 mM for the formation of the (+)‐CSO‐enantiomer and aKm=4.56 mM for the (−)‐CSO‐enantiomer are reported for the first time for FMO1.
Verbal cued recall as a predictor of conversion to Alzheimer's disease in Mild Cognitive Impairment
Authors: Dierckx E. , Engelborghs S. , De Raedt R. , Van Buggenhout M. , De Deyn P. P. , Verté D. , Ponjaert‐Kristoffersen I.
Published: March 2009

Objective

This study was set up to investigate whether neuropsychological tests are able to predict conversion to AD among Mild Cognitive Impairment (MCI) patients.

Methods

At baseline the cognitive part of the Cambridge Examination for Mental Disorders of the Elderly (CAMCOG), the Mini Mental Status Examination (MMSE), the Geriatric Depression Scale (GDS), a Dutch variation of Rey's Auditory Verbal Learning Test, the Memory Impairment Screen plus (MISplus) and the Visual Association Test (VAT) were administered to 40 patients diagnosed with MCI. After 18 months, MCI‐patients were reassessed and a follow‐up diagnosis was established. Of those who were seen for follow‐up (n = 31), seven fulfilled (NINCDS‐ADRDA) criteria of probable AD, while 24 did not convert.

Results

A binary logistic regression analysis showed that the MISplus contributed most to the prediction of conversion (OR = 0.28, 95% CI 0.099–0.790). With a cut‐off of 2 out of 6, a positive predictive value of 71.5%, a negative predictive value of 91.5% and an overall diagnostic accuracy of 87.0% were achieved.

Conclusions

This prospective, longitudinal study shows that a score of 0 or 1 out of 6 on the MISplus may be a good indicator of future (within 18 months) progression to AD among MCI‐patients. Copyright © 2009 John Wiley & Sons, Ltd.
Cidofovir induces an increase in levels of low‐risk and high‐risk HPV E6
Authors: Donne Adam J. , Hampson Lynne , He Xiaotong T. , Rothera Michael P. , Homer Jarrod J. , Hampson Ian N.
Published: March 2009

Background.

Cidofovir is a nucleoside analogue that is used off‐license to treat recurrent respiratory papillomatosis (RRP) caused by HPV6/11. However, the effect of this drug upon low‐risk HPV 6/11 gene expression is unknown.

Methods.

The expression of E6 was evaluated by RT‐PCR in HPV−ve C33A cervical carcinoma cells stably transfected with both low‐ and high‐risk HPV E6 cDNA's and in SiHa (HPV16+ve) cervical carcinoma cells after treatment with 2 doses and durations of exposure to cidofovir.

Results.

Compared to the vector only transcript, E6 RNA levels showed an 8‐fold increase in low‐risk and 20‐fold increase in high‐risk E6‐expressing cells. High‐risk E6 protein levels were also detected by Western blot in cidofovir‐treated C33A Type16 E6‐transfected cells.

Conclusion.

These data may indicate a potential rationale for increased risk of genetic instability and thus transformation due to drug‐induced increase in the level of E6. © 2009 Wiley Periodicals, Inc. Head Neck, 2009
Cotton‐swab cryotherapy for oral leukoplakia
Authors: Yu Chuan‐Hang , Chen Hsin‐Ming , Chang Chia‐Chuan , Hung Hsien‐Yen , Hsiao Chuhsing Kate , Chiang Chun‐Pin
Published: March 2009

Background.

Oral leukoplakia (OL) is a common oral precancerous lesion. Cotton‐swab cryotherapy (CSC) is commonly used for treating skin lesions but is rarely used for treating OL lesions.

Methods.

Sixty OL lesions were treated by CSC once every 2 weeks until complete regression (CR) of the lesion had been achieved.

Results.

CR was achieved in all 60 OL lesions after an average of 6.3 treatments with cryotherapy. The number of CSC treatments required to achieve CR was significantly fewer for OL lesions on oral mucosal sites other than the tongue, those <2 cm2, those with epithelial dysplasia, and those with a surface keratin thickness of <55 μm. Multivariate analyses showed that only the location and area of the OL lesions were independent factors influencing the number of CSC treatments required to achieve CR.

Conclusion.

For OL lesions with a mean surface area of ≤1.8 cm2, CR can be achieved with fewer than 7 CSC treatments on average. CSC is a simple, safe, easy, conservative, and acceptable treatment modality for OL lesions. © 2009 Wiley Periodicals, Inc. Head Neck, 2009
Receptor tyrosine kinases in sinonasal undifferentiated carcinomas—Evaluation for EGFR, c‐KIT, and HER2/neu expression
Authors: Chernock Rebecca D. , Perry Arie , Pfeifer John D. , Holden Joseph A. , Lewis James S.
Published: March 2009

Background.

Our objective was to identify the expression of epidermal growth factor receptor (EGFR), c‐KIT (CD117), and HER2/neu in sinonasal undifferentiated carcinoma (SNUC).

Methods.

Immunohistochemistry for c‐KIT (CD117), EGFR, and HER2/neu was performed on paraffin‐embedded tissue from SNUC cases. A search for activating mutations in c‐kit exons 9, 11, 13, and 17 or gene amplification was undertaken by high‐resolution DNA melting curve analysis and fluorescence in situ hybridization (FISH) for c‐kit and chromosome 4, respectively.

Results.

By immunohistochemistry, 9 of 11 cases (81.8%) were diffusely (4+) positive for c‐KIT, 3 of 11 cases (27.3%) were positive for EGFR, and none of the cases were positive for HER2/neu. Neither activating mutations nor gene amplification of c‐kit were detected in any of the 8 assessable tumors.

Conclusion.

c‐KIT is frequently expressed in SNUC. However, the overexpression is not due to activating mutations or gene amplification. © 2009 Wiley Periodicals, Inc. Head Neck, 2009
Neuronal circuit‐dependent alterations in expression of two isoforms of glutamic acid decarboxylase in the hippocampus following electroconvulsive shock: A stereology‐based study
Authors: Jinno Shozo , Kosaka Toshio
Published: March 2009

There is an increasing body of evidence suggesting that GABAergic dysfunction is involved in various psychiatric disorders. The goal of our study was to investigate the influences of electroconvulsive therapy (ECT), one of the most effective treatments for depression, on the GABAergic system in the hippocampus. In this stereology‐based study, we identified GABAergic neurons by immunostaining for two isoforms of glutamic acid decarboxylase (GAD), GAD65, and GAD67 and estimated the expression changes induced by single or repeated electroconvulsive shock (ECS; an animal model of ECT). The numerical density (ND) of entire population of GABAergic neurons (expressing GAD65 and/or GAD67) was seldom altered by the administration of ECS. GAD67‐positive (GAD67+) neurons were also rarely affected by ECS. On the other hand, the ND of GAD65+neurons was changed in a layer‐specific manner. In the CA1 region, the ND of GAD65+neurons was increased in the strata radiatum/lacunosum‐moleculare (SR/SLM) by repeated ECS. In the CA3 region, the ND of GAD65+neurons was decreased in the stratum oriens and SR/SLM after single ECS. The expression ratio of GAD65 in GABAergic neurons was increased specifically in layers receiving afferents from the entorhinal cortex (EC), i.e., SR/SLM of the CA1 region and molecular layer of the dentate gyrus (DG), after repeated ECS administration, whereas the expression ratio of GAD67 in GABAergic neurons was decreased in several layers by the same treatment. These results indicate that the ECS‐induced changes in ND of GAD65+or GAD67+neurons were most likely due to alterations in GAD expression rather than actual increases or decreases in cell numbers. Altogether, the neuronal circuit‐dependent alterations in GABA‐mediated signaling may play a contributory role in the depression treatment process introduced by ECT. © 2009 Wiley‐Liss, Inc.
Training's woeful countenance
Authors: Kopp David M. , Desiderio Katie P.
Published: March 2009

In this article, we explore how the folk science of physiognomy shaped the training given to salesmen in the early 20th century. In reviewing training and vocational counseling manuals from the past and using them as cultural artifacts, one can put forth the theme that the field of training and development advances only through critical reflection—specifically, questioning training's role within a broader context including issues of social justice. Lessons learned here include the recurring idea that we, in human resource development (HRD), must be vigilant in ensuring that not only are training outcomes ethical but so too are the interventions.
Competencies needed by Korean HRD master's graduates: A comparison between the ASTD WLP competency model and the Korean study
Authors: Lee Yonghak
Published: March 2009

The primary purpose of this study was to identify competencies needed by current human resource development (HRD) master's degree graduate students in Korea. The study used a quantitative method, the Delphi technique, in combination with a qualitative method consisting of a series of in‐depth interviews. The Delphi technique was conducted using a survey questionnaire instrument based on a list of competencies analyzed by means of median scores and standard deviation that was developed for the ASTD study. The in‐depth interviews were conducted with the Delphi panelists. The study found that both faculty and professional respondents rated all the ASTD competencies as quite important, and there were considerable gaps between the importance and expertise level of each competency for Korean HRD master's graduates. In the qualitative portion of the study, respondents suggested several additional competencies that were relevant to the Korean cultural context.
Differential mRNA expression of acetylcholinesterase in the central nervous system of rats with acute and chronic exposure of sarin & physostigmine
Authors: Bansal Iti , Waghmare C. K. , Anand T. , Gupta A. K. , Bhattacharya B. K.
Published: March 2009

A time‐course study was carried out to measure the acetylcholinesterase (AChE) gene expression in the brain of female rats exposed to different doses of sarin and physostigmine. Short‐term effects were studied with an acute single subcutaneous dose (s.c.) of 80 µg kg−1(0.5 × LD50) sarin. Cortex and cerebellum showed a significant decline in AChE mRNA expression at 2.5, 24 and 72 h. Biochemical studies showed that plasma butrylcholinesterase (BChE) and brain AChE activities were significantly decreased at 2.5 h, which came back to near control values by 24 h in both cases. For long‐term chronic studies, three groups of female rats received daily doses of physostigmine (0.1 mg kg−1 day−1) intramuscularly (i.m.), sarin (15 µg kg−1 day−1) s.c. independently and a combined dose of physostigmine (i.m.) (0.1 mg kg−1 day−1) followed by sarin (s.c.) (15 µg kg−1 day−1) continuously for 30 days. Differential AChE mRNA levels in cortex and cerebellum of rat brain were observed after 30 days and after a lag period of another 30 days with no further administration. Plasma (BChE) and brain (AChE) showed irregular inhibition profile in biochemical studies at 30 days and returned to control levels after 60 days. The acute single subcutaneous administration of sarin for short‐term as well as chronic long‐term studies showed that AChE inhibition alone does not lead to observed changes in mRNA expression of AChE gene. These observations further suggest that route of administration as well as dose exposure regimen also contributes to the regulation of AChE mRNA expression. Copyright © 2009 John Wiley & Sons, Ltd.
Collagen vitrigel membranes for the in vitro reconstruction of separate corneal epithelial, stromal, and endothelial cell layers
Authors: McIntosh Ambrose Winnette , Salahuddin Afrah , So Stephen , Ng Shengyong , Ponce Márquez Sara , Takezawa Toshiaki , Schein Oliver , Elisseeff Jennifer
Published: March 2009

The goal of this study was to evaluate the potential suitability of collagen Vitrigel (CV) membrane as a substrate for the separate reconstruction of the three main cellular layers of the cornea. Limbal explants, keratocytes, and endothelial cells were cultured on transparent membranes made of type I collagen. The resulting cell sheets were evaluated using RT‐PCR, in addition to light and electron microscopy. Tensile testing was also performed to examine the mechanical properties of CV. Limbal explant cultures resulted in partially stratified epithelial sheets with upregulation of the putative stem cell marker p63. Keratocytes cultured in serum on CV exhibited stellate morphology along with a marked increase in expression of corneal crystallin ALDH and keratocan, (a keratan sulphate proteoglycan: KSPG), compared to identical cultures on tissue culture plastic. Endothelial cells formed dense monolayers with uniform cell size, tight intercellular junctions, and expression of voltage‐dependent anion channels VDAC2 and VDAC3, chloride channel protein CLCN2, and sodium bicarbonate transporter NBC1. Epithelial and endothelial cells exhibited adhesive structures (desmosomes and hemidesmosomes) and evidence of apical specialization (microplicae), while endothelial cells also produced a Descemet's membrane‐like basal lamina. CV was found to possess ultimate tensile strengths of 6.8 ± 1.5 MPa when hydrated and 28.6 ± 7.0 MPa when dry. Taken together, these results indicate that CV holds promise as a substrate for corneal reconstruction. © 2009 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater, 2009
Comparison of B‐scan sonographic measurements of optic cup with fundus photographic measurements
Authors: Ali Nadir Ali Mohamed , Subrayan Visvaraja , Reddy Sagili Chandrasekhara , Othman Faizah
Published: March 2009

Purpose.

To compare the measurements of the optic cup diameter with B‐scan sonography with fundus photography in patients with clear ocular media and to propose a solution for the clinical problem of determining the cup‐disc ratio in eyes with opaque ocular media.

Methods.

We studied 122 patients (glaucoma patients and non‐glaucoma controls) with clear ocular media. Measurements of optic cup diameters using Quantel 10 MHz B‐scan sonography were compared with magnification‐corrected measurements of the same area using Zeiss FF450 Plus fundus camera. Paired‐sample t‐test was used to compare the measurements. The correlation between measurements of optic cup diameters using the 2 methods was established. In addition, the optic disc diameters of both eyes were measured on fundus photographs and compared with each other.

Results.

There was no significant difference between the fundus photographic and sonographic measurements of optic cup diameters. There was no difference in the fundus photographic measurements of optic disc diameters between the 2 eyes.

Conclusion.

In an eye with opaque ocular media, the cup‐disc ratio can be calculated by using the optic cup diameter of this eye with B‐scan sonography and the optic disc diameter of the fellow eye with clear media measured by fundus photography. © 2009 Wiley Periodicals, Inc. J Clin Ultrasound 2009
Biliary dilatation secondary to lithiasis in a child affected by Langerhans' cell histiocytosis
Authors: Caruso Settimo , Miraglia Roberto , Spada Marco , Luca Angelo , Gridelli Bruno
Published: March 2009

Langerhans' cell histiocytosis (LCH) is a disease of unknown pathogenesis, caused by clonal proliferation of Langerhans' cells. Liver involvement results in a cholangiopathy, which has the radiologic appearance of sclerosing cholangitis. Only 1 case of obstructive jaundice due to common bile duct stone in a patient with LCH has been described. We present a case of a 31‐month‐old child with LCH and liver involvement on the waiting list for liver transplantation. During the follow‐up, there was a rapid onset of jaundice due to sludge and lithiasis. The patient was treated first with an endoscopic biliary plastic stent and then with percutaneous biliary drainage and bilioenteric anastomosis. © 2009 Wiley Periodicals, Inc. J Clin Ultrasound 2009
Spermatozoal RNAs: What about their functions?
Authors: Dadoune Jean‐Pierre
Published: March 2009

The profound architectural changes that transform spermatids into spermatozoa result in a high degree of DNA packaging within the sperm head. However, the mature sperm chromatin that harbors imprinted genes exhibits a dual nucleoprotamine/nucleohistone structure with DNase‐sensitive regions, which could be implicated in the establishment of efficient epigenetic information in the developing embryo. Despite its apparent transcriptionally inert state, the sperm nucleus contains diverse RNA populations, mRNAs, antisense and miRNAs, that have been transcribed throughout spermatogenesis. There is also an endogenous reverse transcriptase that may be activated under certain circumstances. It is now commonly accepted that sperm can deliver some RNAs to the ovocyte at fertilization. This review presents potential links between male‐specific genomic imprinting, chromatin organization, and the presence of diverse RNA populations within the sperm nucleus and discusses the functional significance of these RNAs in the spermatozoon itself and in the early embryo following fertilization. Some recent data are provided, supporting the view that analyzing the profile of spermatozoal RNAs could be useful for assessment of male fertility. Microsc. Res. Tech. 2009. © 2009 Wiley‐Liss, Inc.
Sulfamic acid catalyzed one‐pot synthesis of 2,5‐diaryl‐1,3,4‐oxadiazoles under microwave irradiation and conventional heating
Authors: Madhav J. Venu , Reddy Y. Thirupathi , Reddy P. Narsimha , Crooks Peter. A. , Kumar V. Naveen , Rajitha B.
Published: March 2009

magnified image

Sulfamic acid has been found to be an efficient catalyst for the one‐pot synthesis of novel 2,5‐diaryl‐1,3,4‐oxadiazoles by condensation of different coumarinoyl hydrazides with various coumarinoyl or quinolinoyl chlorides under microwave irradiation and conventional heating. Some of the advantages of this method are low reaction times, operational simplicity, and high yields. J. Heterocyclic Chem., (2009)
Amodiaquine N‐oxides and other 7‐chloro‐4‐aminoquinoline n‐oxides
Authors: Elslager Edward F. , Gold Eva H. , Tendick Frank H. , Werbel Leslie M. , Worth Donald F.
Published: March 2009

Oxidation of amodiaquine with perbenzoic acid gave amodiaquine N‐α‐oxide, whereas N4‐methylamodiaquine and amodiaquine 1‐oxide afforded N4‐methylamodiaquine N‐α,1‐dioxide and amodiaquine N‐α, 1‐dioxide, respectively. Amodiaquine 1‐oxide, O‐methyl‐amodiaquine 1‐oxide, oxychloroquine 1‐oxide, and a variety of other 4 ‐ (7‐chloro‐4‐quinolylamino)‐α‐dialkylamino‐o‐cresol 1‐oxides and 7‐chloro‐4‐[(mono‐ and dialkylamino)‐alkylamino]quinoline 1‐oxides were prepared by the condensation of 4, 7‐dichloroquinoline 1‐oxide with a 4‐amino‐α‐(dialkylamino)‐o‐cresol, N‐α, N‐α‐diethyl‐6‐methoxytoluene‐α, ‐3‐diamine, or a mono‐ or dialkylaminoalkylamine in phenol or aqueous ethanol. N4‐Methyl‐amodiaquine was synthesized from p‐ [(7‐chloro‐4‐quinolyl)methylamino]phenol, diethyl‐amine, and paraformaldehyde. Many of the N‐oxides are highly active against the plasmodia of malaria.
Studies directed toward the total synthesis of novel azasteroids. III. The formation of a hexahydroisoquinoline, octahydroisoquinoline and a decahydro‐2h‐benzo[a]quinolizine as precursors to 8‐azasteroids
Authors: Meyers A. I. , Betrus B. J. , Ralhan N. K. , Rao K. Babu
Published: March 2009

A plan of approach to novel 8‐azasteroids was tested with suitable model compounds to determine its feasibility. The results of these experiments are described.
Pteridine XXIX Über die synthese von pteridin ‐7‐0‐ und ‐n‐8‐glucosiden
Authors: Pfleiderer Wolfgang , Söil Dieter
Published: March 2009

Es wird über die erstmals gelungenen Synthesen der beiden möglichen O‐ und N‐Gluco‐side eines 7‐Hydroxypteridins berichtet. Die Direktglucosidierung des 4‐Dimethylamino‐7‐hydroxypteridins mit Acetobromglucose führte zum 4‐Dimethylamino‐7‐(2. 3.4. 6‐tetra‐acetyl‐β‐D‐glucopyranosyloxy)pteridin während die Darstellung des isomeren 8‐(2.3.4.6‐Tetraacetyl‐β‐D‐glucopyranosyl)‐4‐dimethylamino ‐7‐oxo‐ dihydropteridins nur ausgehend vom 4‐Amino‐6‐dimethylaminopyrimidin und Glucosidierung auf der Pyrimidinstufe re‐alisiert werden konnte. Die Pteridin‐glucoside wurden durch UV‐Absorptionsspektren, Drehwerte und Hydrolyseversuche charakterisiert.
Fluoro derivatives of phenarsazine
Authors: Thu‐Cuc S. T. , Buu‐Hoi N. P. , Xuong N. D.
Published: March 2009

Several fluorinated derivatives of phenarsazine and benzophenarsazines, bearing various additional substituents in their molecule, have been prepared from arsenic trichloride and the appropriate N, N'‐diarylamines. These compounds showed strong irritant and sternutatory properties.
Aeridizinium derivatives having meta‐directing substituents
Authors: Bradsher C. K. , Parham J. C.
Published: March 2009

Through cyclization of suitably substituted 1‐benzyl‐2 ‐ (1, 3‐ dioxolan‐2‐yl)pyridinium salts, ačeridizinium salts having nitro, carboxyl or sulfo substituents have been prepared. The 9‐sulfo aeridizinium derivative exists as a remarkably stable betaine.
N‐acyl derivatives of ϵ‐caprolactam
Authors: Donaruma L. Guy , Scelia Richard P. , Schonfeld Steven E.
Published: March 2009

The preparation and properties of a number of new N‐acylcaprolactams are described. These compounds were found to be catalysts for the anionic polymerization of caprolactam.
Mass spectra of furoxans
Authors: Ungnade H. E. , Loughran E. D.
Published: March 2009

The mass spectra of furoxans have large NO+ peaks due to the fragmentation of the ring system at C‐N and N‐O bonds. Cleavage of the substituents and to a smaller extent ring fission at C3‐C4 account for other ion peaks. The spectra are sufficiently characteristic to serve for the identification of these compounds. The related furazans give different fragmentation patterns because carbon‐carbon cleavage predominates.
A new synthesis of 3‐chloroflavones
Authors: Newman Melvin S. , Ferrari John L. , Garg C. P.
Published: March 2009

The synthesis of a number of 3‐chloroflavones by a new method, involving reaction of arylmagnesium bromides with 3,4‐dichlorocoumarins, is described. The synthesis of 2‐chloro‐7‐methyl‐11H‐benzofuro[3,2‐b] [1)benzopyran‐11‐one is also described.
Analogs of tetrahydrofolic acid. XII. On the relative contribution by the 2‐amino and 4‐hydroxy groups of 2‐amino‐5‐(3‐anilinopropyl)‐6‐methyl‐4‐pyrimidinol to inhibition of folic reductase and thymidylate synthetase
Authors: Baker B. R. , Ho Beng‐Thong , Neilson Thomas
Published: March 2009

The structure of 2‐amino‐5‐(3‐anilinopropyl)‐6‐methyl‐4‐pyrimidinol (II), an inhibitor of both dihydrofolic reductase and thymidylate synthetase, has been modified by replacement of the 2‐amino group by hydrogen or the 4‐hydroxyl group by hydrogen, mercapto or amino. Enzymic evaluation showed that 5‐(3‐anilinopropyl)‐2,4‐diamino‐6‐methyl‐pyrimidine was a 170‐fold more effective inhibitor of dihydrofolic reductase than thymidylate synthetase. This specificity is due to the fact that replacement of the 4‐hydroxyl group of II with 4‐amino enhances binding to dihydrofolic reductase by 350‐fold, but binding to thymidylate synthetase is unchanged. No significant cross‐over specificity was noted with the six compounds studied.

Replacement of the 4‐hydroxyl group of II by hydrogen gave a compound (XVII) that was a slightly more effective inhibitor of dihydrofolic reductase than II, but was slightly less effective on thymidylate synthetase. Binding to dihydrofolic reductase and to thymidylate synthetase could be increased by 17‐fold and 5‐fold, respectively, by replacement of the 4‐hydroxyl group of II by 4‐mercapto (XVI). It was concluded that the mode of binding in the N‐3 and 4‐hydroxyl region of II was not the same for the two enzymes.

Synthesis of the 2‐amino‐, the 4‐hydroxy‐ and the 4‐mercaptopyrimidyl analogs of II are described. Also described are the partial purification of and assays for dihydrofolic reductase and thymidylate synthetase by procedures more familiar to the organic chemist.
3‐Oxazolines
Authors: Gaines Jack R. , Hansen Gary R.
Published: March 2009

α‐Hydroxy‐α‐methyl ketones react with ammonia and aromatic aldehydes in the presence of calcium chloride and ammonium chloride to yield 2‐aryl‐3‐oxazolines.
Azasteroids. I. A convenient synthesis of ethyl 1,2,3,3‐tetrahydrohenzo[f] quinoline‐3‐carboxylate
Authors: Popp Frank D. , Schleigh William R.
Published: March 2009

In view of the fact that a synthesis of 3‐desoxy‐18‐nor‐14‐azaequilenin (I) has recently been reported (3) we wish to report on our synthetic path to this azasteroid. In this work the intermediate ethyl 1,2,3,4‐tetrahydrobenzo[f]quinoline‐3‐carboxylate (II) was conveniently synthesized from commercially available benzo[f]quinoline (III). Compound III was converted to the Reissert compound (IV) (4), which on hydrolysis (5) gave the acid V. Catalytic hydrogenation of V gave poor results when carried out in glacial acetic acid or 15% hydrochloric acid at room temperature. However, the reduction proceeded smoothly and quantitatively by the procedure indicated in the experimental. Esterification of the crude, reduced acid hydrochloride (VI) proceeded to give II which can be converted into I as described (3).
The synthesis of 2,2 and 5,5 ‐bi(1,10‐phenanthroline)
Authors: Case Francis H.
Published: March 2009

The well‐known chelating ability of 1,10‐phenanthroline and its derivatives for Fe(II) and Cu(I) have prompted the synthesis of 5, 5′‐bi(1, 10‐phenanthroline) (I) and 2, 2′‐bi(1, 10‐phenanthroline (II).
Spiranes. V. A synthetic route to symmetrical and unsymmetrical 3,9‐diazaspiro [5.5]undecanes
Authors: Rice Leonard M. , Grogan Charles H. , Freed Meier E.
Published: March 2009

The synthesis of derivatives of the hitherto unreported 3,9‐diazaspiro[5,5]undecane has been accomplished. Starting from the dianhydride of methanetetraacetic acid or from N‐methyl‐4‐piperidone, synthetic paths have been developed which permit the preparation of either symmetrical or unsymmetrical derivatives.
The chemistry of triazine derivatives. I. The alkylation of 2,4,6‐trimethyl‐s‐triazine
Authors: Osborne David R. , Levine R.
Published: March 2009

The direct alkylation of 2,4,6‐trimethyl‐s‐triazine (I) has been effected by treating (I) with a series of alkyl halides using potassium amide in liquid ammonia as the condensing agent. The present method gives a simple, direct route to the preparation of unsymmetrically substituted trialkyl‐s‐triazines.
N‐(2‐benzoxazolyl)anthranilic acid and 3‐(2‐hydroxyphenyl)‐quinazoline‐2,4‐dione
Authors: Sam Joseph , Richmond Charles W.
Published: March 2009

The hydrolysis of 12H‐benzoxazolo[2,3‐b]quinazolin‐12‐one (I) yields N‐(2‐benzox‐azolyl)anthranilic acid (III) and 3‐(2‐hydroxyphenyl)quinazoline‐2,4‐dione (IV). Unequivocal syntheses of both III and IV are described.
The acylation of 2‐picoline‐N‐oxide and 2,6‐lutidine N‐oxide
Authors: Osborne David R. , Levine Robert
Published: March 2009

2‐Picoline N‐oxide and 2,6‐Lutidine N‐oxide have been acylated in good to high yields by reaction with a series of aliphatic, aromatic and heterocyclic esters using sodium amide in liquid ammonia as the condesing agent.
A high‐yield modification of the baker‐venkataraman rearrangement. Application to the synthesis of 5‐hydroxyflavone and 6,8‐dichloro‐5‐hydroxyflavone
Authors: Looker J. H. , Edman James R. , Dappen J. I.
Published: March 2009

A three‐step synthesis of 5‐hydroxyflavone in 80% yield from 2,6‐dihydroxyaceto‐phenone is described. The key step is a modification of the Baker‐Venkataraman rearrangement in which small amounts of water are deliberately introduced. Characterization of the primary rearrangement products, 1‐(2,6‐dinydroxyphenyl)‐3‐phenyl‐1,3‐propane‐dione, and 1‐(2‐benzoyloxy‐6‐hydroxyphenyl)‐3‐phenyl‐1,3‐propanedione, is reported. Application of the synthesis to 3,5‐dichloro‐2,6‐dihydroxyacetophenone gives a mixture of 6,8‐dichloro‐5‐hydroxyflavone and its 3‐benzoyl derivative. Infrared spectral data are presented for several intermediates and flavones, and indicate the utility of the previously described infrared spectral method for detecting 3‐aroylflavones.
The chemistry of pyrazine and its derivatives. IX The pyrazylethylation of amines
Authors: Singerman Gary M. , Levine Robert
Published: March 2009

A series of pyrazylethylated derivatives of the type C4H3N2CH2CH2N= has been prepared in high yields by the reactions of vinylpyrazine with amines using methanolic acetic acid or metallic sodium as the catalyst.
14H‐Indolo[2,3‐a]phenanthridizinium Salts
Authors: Bradsher C. K. , Litzinger E. F.
Published: March 2009

Four l‐Aryl‐9H‐[3,4‐b]pyridoindoles have been prepared and quaternízed with bromoacetone. The resulting salts were cyclized under acidic conditions to afford 5‐methyl‐14H‐indolo[2,3‐a]phenanthridizinium perchlorate as well as the 2,3‐dimethoxy‐, 2,3‐methylenedioxy‐ and 2‐methoxy‐ derivatives.
New derivatives of ϵ‐caprolactam
Authors: Reimschuessel Herbert K.
Published: March 2009

The synthesis of α ‐ (carbethoxyvinyl)caprolactam (V) is reported. This synthesis involves condensation of α‐bromocaprolactam with diethyl malonate, semi‐hydrolysis of the malonic ester derivative, and a Mannich reaction on the product of the latter reaction. All of the intermediate compounds and some of the by‐products are new derivatives of ϵ‐caprolactam. Their infrared and n.m.r. spectra are recorded.
Imidazole‐catalyzed hydrolysis of acetoxyflavones physical and chemical properties of hydroxyflavones. III
Authors: Looker J. H. , Holm Myron J. , Minor J. L. , Kagal S. A.
Published: March 2009

A method for the hydrolysis of acetoxyflavones with catalytic amounts of imidazole in 60% ethanol or 60% methanol is described. The method has been applied to the acetates of monohydroxyflavones, polyhydroxyflavones, and the trihydroxyflavones naringenin and hesperetin. Partial deacetylation of quercitrin heptaacetate is described. The methane‐sulfonates of several monohydroxyflavones, and the stability of flavonol methanesulfonate in the imidazole‐ethanol reagent are reported.
Difluorodiazirine. IV. Synthesis of substituted perfluorocyclopropanes
Authors: Mitsch Ronald A.
Published: March 2009

The preparation of eight previously undisclosed substituted perfluorocyclopropanes by the addition of difluorocarbene to the respective fluorocarbon olefins is described. The yields, generally 30‐85%, are dependent upon the reaction temperature, the amount of excess olefin and the nature of the groups present in the fluoroolefin.
N,N'‐carbonyldiimidazole as a reagent for the preparation of five‐membered heterocycles
Authors: Wright William B.
Published: March 2009

Derivatives of 2‐benzimidazolinone, 2‐imidazolidinone, and 2‐oxazolidinone are obtained in good to excellent yield when the appropriate diamine or aminoalcohol is allowed to react with N, N'‐carbonyldiimidazole.
Crystal and molecular structure of 7‐(p‐lodobenzenesulfonyl)‐7‐azabicyclo 4.1.0 heptane
Authors: Trefonas L. M. , Majeste Richard
Published: March 2009

The structure of 7‐(p‐iodobenzenesulfonyl)‐7‐azabicyclo[4.1.0]heptane has been determined by a three dimensional single‐crystal x‐ray diffraction study. The compound crystallizes in the monoclinic space group P/n with cell dimension a0 = 10.35 ± .005, b0 = 16.33, c0 = 8.22 Å and a monoclinic angle, β = 99°40° ± 5′. The aziridine ring is fused cis to the cyclohexane ring with fusion angles of 122°. The cyclohexane ring is flattened appreciably, although still in the chair conformation. Bond distances within the cyclohexane ring are shortened to an average value of 1.49 Å. The p‐iodobenzene‐sulfonate group is at an angle of 98. 3° to the bicyclic system containing the aziridine and cyclohexane fused rings. A final value of R = 0. 115 was obtained for the 1272 independent reflections.
Die kristall und molekulstrük tur des 2,3,7,8‐tetrachlorphenazins
Authors: Riganti Vincenzo , Locchi Stelio , Curti Renato , Bovio Bruno
Published: March 2009

Die Kristall‐ und Molekülstruktur des 2, 3, 7, 8‐Tetrachlorphenazins C12H4N2Cl4 wurde roentgenographisch bestimmt. Die Kristalle enviesen sich als omonoklin, Raumgruppe P/c, und ergaben folgende Gitterkonstanten: a0 = 3.85 ± 0.02 Å, b0 = 6. 04 ± 0.02 Å, c0 = 25.33 ω 0.04 Å, β = 91° 46′ ± 15′. Das Molekül ist planar innerhalb der experimentellen Fehlergrenzen; alle intermolekularen Abstände stimmen mit denjenigen aus den van der Waals'schen Radien überein.
Synthesis and properties of fluorine‐containing heterocyclic compounds. I. trifluoromethyl quinolines
Authors: Dey Adrienne Steinacker , Joullié Madeleine M.
Published: March 2009

The condensation of ethyl trifluoroacetoacetate with various aromatic amines, in polyphosphoric acid at 150°, gave substituted 2‐trifluoromethyl‐4‐quinolinols. The structure of these compounds was established from a study of their infrared and ultraviolet spectra and, in some cases, by independent synthesis and cyclization of the intermediate 3‐arylaminocrotonates. The 2‐trifluoromethyl‐4‐quinolinols were converted to 2‐trifluoromethyl‐4‐chloroquinolines which were subjected to hydrogenolysis with Raney nickel to yield 2‐trifluoromethylquinolines and to treatment with an excess of hydrazine to give the corresponding hydrazino derivatives. The diazotization of 2 ‐ trifluoromethyl ‐4‐hydrazinoquinolines yielded azides which were unusually stable. The infrared and ultraviolet spectra of some of the compounds prepared are discussed.
Synthesis and properties of fluorine‐containing heterocyclic compounds. II. trifluoromethyl benzo[h]quinolines, benzo[h]‐1,6‐napthyridines, 1,7‐ and 1,10‐phenanthrolines
Authors: Dey Adrienne Steinacker , Joullié Madeleine M.
Published: March 2009

Four heterocyclic rings containing the trifluoromethpl group have been prepared by the reductive, dehalogenation of the corressponding chloro compounds. These were obtained from the hydroxy derivativexs which, in turn, were formed in the condensation of ethyl trifluoroacetoacetate with 1‐naphthylaminc and some substituted aminoquinolines. Spectral data were used to ascertain the position of the hydroxyl group in the hydroxy derivatives. In one case, the position of this group was established by an independent synthesis.
Synthesis of 6, 13‐diazadibenz [a,h] anthracene
Authors: Klemm L. H. , Weisert Annekäte
Published: March 2009

6,13‐Diazadibenz[a,h]anthracene (XIa) was synthesized in 15% overall yield for four steps beginning with 2, 5‐diphenyl‐1,4‐benzoquinone. Miscellaneous reactions which led to side products are also described.
Pyridoxine chemistry. VIII. synthesis of 5‐norpyridoxol
Authors: Korytnyk W. , Paul B.
Published: March 2009

5‐Norpyridoxol (3,5‐dihydroxy‐4‐hydroxymethyl‐6‐methylpyridine, I) has been synthesized. In contrast to the other two isomeric norpyridoxols (II and III), it proved to be inhibitory to Saccharomyces carlsbergensis. Improved methods of synthesis for some intermediates previously described have been developed.
The preparation of some fluorobenzothiasoles
Authors: Roe Arthur , Tucker William P.
Published: March 2009

The seven possible monofluoro‐2‐phenylbenzothiazoles have been prepared. Each was prepared by potassium hexacyanoferrate(III) oxidation of the appropriately substituted thiobenzanilide. Several were also prepared via a benzyne intermediate through treatment of suitable thiobenzanilides with potassium amide and liquid ammonia.
Quinazolines II. metal hydride reductions
Authors: Smith Richard F. , Briggs Paul C. , Kent Ronald A. , Albright James A. , Walsh Edward J.
Published: March 2009

The following sodium borohydride reductions are reported: 3‐methylquinazolium iodide (I) or its methanolate (II) → Nα, Nα‐dimethyl‐α, 2‐toluenediamine; quinazoline → 3,4‐dihydroquinazoline or 1,2,3,4‐tetrahydroquinazoline (V). The following lithium aluminum hydride reductions are reported: I or II → 3‐methyl‐l,2,3,4‐tetrahydroquinazoline; quinazoline → V + Nα ‐methyl‐α, 2‐toluenediamine (VI); 4 ‐ chloroquinazoline → VI; 2‐chloroquinazoline → VI; 2,4 ‐ dichloroquinazoline → V; 2‐chloro‐4‐phenylquinazo‐ line → 4‐phenyl‐3,4‐dihydroquinazoline; 2‐phenyl‐4‐chloroquinazoline → 2‐phenyl‐3,4‐dihydroquinazoline or Nα ‐ benzyl‐α, 2 ‐ toluenediamine; 4 ‐ methoxyquinazoline → 4‐methoxy‐l,2‐dihydroquinazoline; 4‐phenoxyquinazoline → 4‐phenoxy‐l,2‐dihydroquinazoline; 4‐thiophenoxyquinazoline → VI.
The aldol condensation of aromatic aldehydes with n‐acetyl‐2‐pyrrolidinone: Synthesis of 3‐arylidene‐2‐pyrrolidinones
Authors: Zimmer Hans , Armbruster David C. , Trauth L. J.
Published: March 2009

The synthesis of several 3‐arylidene‐2‐pyrrolidinones (V) by aldol condensation between aromatic aldehydes and N‐acetyl‐2‐pyrrolidinone is reported. The UV‐spectra of structures of type V compounds are discussed and compared with those of the corresponding α ‐arylidene‐γ‐butyrolactones.
Nucleosides XXVIII. 3′‐amino‐3′ ‐deoxyhexopyranosyl nucleosides. Part III. Synthesis of 3′‐amino‐3′‐deoxyhexopyranosyl adenines
Authors: Beránek J. , Friedman H. A. , Watanabe K. A. , Fox J. J.
Published: March 2009

Treatment of adenosine with metaperiodate followed by condensation with nitromethane yielded a mixture or 3′‐deoxy‐3′‐nitrohexopyranosyl adenines which were converted to 3′‐amino‐3′‐deoxyhexopyranosyl nucleosides. Separation of this mixture followed by acetylation yielded three crystalline isomeric 9‐(3′‐acetamido‐3′‐deoxy‐2′,4′, 6′‐tri‐O‐acetyl‐β‐D‐hexosyl)adenines which were proved by chemical and n. m. r. studies to be the manno (VII), gulacto (X) and gluco (XIII) derivatives.
The synthesis of various chloroimidazo[4,5‐c]pyridines and related derivatives
Authors: Rousseau Robert J. , Robins Roland K.
Published: March 2009

A new and convenient route to the synthesis of 4‐chloroimidazo[4,5‐c]pyridine (IV) has been devised. The preparation of 6‐chloroimidazo[4,5‐c]pyridine (IX) and 4,6‐dichloroimidazo[4, 5‐c]pyridine (XX) has been accomplished for the first time by ring closure of the requisite Chloro‐3.4‐diaminopyridines with ethyl orthoformate and acetic anhydride. Ring closure of 2,4,5‐triaminopyridine (XI) with ethyl orthoformate and acetic anhydride gave 6‐aminoimidazo[4, 5‐c]pyridine (XII). Imidazo[4, 5‐c]pyridine‐4‐thione (XXI has been prepared from 4‐chloroimidazo[4, 5‐c]pyridine.
The synthesis and some reactions of 2‐methyl‐4,5‐pyrimidinediearbonitrile
Authors: Schwan Thomas J. , Tieckelmann Howard
Published: March 2009

Diethyl ethoxymethyleneoxalacetate and acetamidine gave 2‐methyl‐4,5‐bis(carbethoxy)‐pyrimidine. The ester was converted to 2‐methyl‐4, 5‐pyrimidinedicarbonitrile which gave 2‐methyl‐4‐methoxy‐5‐pyrimidinecarbonitrile when treated with methanol at room temperature. Attempts to hydrogenate the dinitrile in the presence of nucleophiles led to displacement at C‐4. Attempted hydrogenation of the dinitrile in dimethylformamide gave 2,2′‐dimethyl‐5, 5′‐dicyano‐4, 4′‐bipyrimidine.
Intramolecular diels‐alder cyclization into the thiophene ring
Authors: Kiemm L. H. , Gopinath K. W.
Published: March 2009

Trans‐3‐(2‐ and 3‐thienyl)allyl alcohols have been prepared from the corresponding acroleins. The esters of these alcohols with phenylpropiolic acid underwent intramolecular Diels‐Alder reactions to give the substituted dihydrothianaphthene lactones Va and Vb, respectively.
The synthesis and structure of methyl‐ and dimethylthiazoloquinolines
Authors: Di Modica Gaetano , Borni Ermanno , Monache Franco Delle
Published: March 2009

The preparations and properties of new methyl‐ and dimethylthiazoloquinolines are described. The NMR evidence supports the angular structures of these heterocycles.
1‐Substituted phenothiazine derivatives
Authors: Driscoll John S. , Nealey Richard H.
Published: March 2009

Several new 1‐substituted phenothiazine derivatives have been synthesized and characterized. A 1‐carboxythionine dye is described.
Characterization of Nx,Ny‐Disubstituted adenines by ultraviolet absorption spectra
Authors: Leonard Nelson J. , Carraway Kermit L. , Helgeson John P.
Published: March 2009

By the synthesis of representative Nx,Ny‐dibenzyladenines and determination of their ultraviolet absorption spectra in acidic, basic and neutral solution we have assembled a body of spectral characteristics which makes it possible to distinguish among possible N,N‐disubstituted adenines.
Synthesis of thiophene isosters of benzacridines and dibenzacridines from hydroxy‐ and amino‐thianaphthenes
Authors: Ricci A. , Buu‐Hoi N. P. , Jacquignon P. , Dufour M.
Published: March 2009

In the Ullmann‐Fetvadjian synthesis of dibenzacridines (thermal condensation of a naphthol with a naphthylamine in the presence of paraformaldehyde), 5‐hydroxy‐3‐methyl‐thianaphthene and 3‐phenyl‐5‐aminothianaphthene behave like β‐naphthol and β‐naphthylamine respectively; several analogs of the carcinogenic dibenzacridines, bearing both nitrogen‐ and sulfur‐heteroatoms, have thus been prepared. 3‐Hydroxythianaphthene, which fails to undergo an Ullmann‐Fetvadjian reaction with aniline, readily does so with 4‐aminobiphenyl.
Organic fluoronitrogens. IV. Halo‐Diazirines
Authors: Mitsch Ronald A. , Neuvar Erwin W. , Koshar Robert J. , Dybvig Douglas H.
Published: March 2009

The physical and spectral properties of five previously undisclosed diazirines substituted with electron‐withdrawing groups are described. The halo‐diazirines yield the respective divalent carbon species and nitrogen on pyrolysis. The cyanofluoro‐, fluoro‐methoxy‐ and fluorodifluoramino‐carbenes form the respective cyclopropanes with tetra‐fluoroethylene. The intramolecular reactions of difluoramino‐substituted carbenes are also discussed. The ultraviolet spectra are presented.
Heterocyclic azonia derivatives including new spiro ring systems
Authors: Cossar Bernard C. , Reynolds Delbert D.
Published: March 2009

A variety of heterocyclic azonia derivatives have been prepared by reaction of alkoxy‐methylamines with haloalcohols and haloalkylthiols. Many of these represent new heterocyclic azoniaspiro ring systems. Evidence has been presented for structural assignments.
Pyridazines. III. The synthesis of substituted pyridazines
Authors: Castle Raymond N. , Kaji Kenji
Published: March 2009

A series of pyridazines and pyridazones have been prepared substituted with alkyl, alkoxyl, halogen, mercapto, substituted mercapto, phenyl, morpholino, piperidino, styryl, substituted styryl and pyridylethenyl groups as potential antitumor agents. The compounds possessing antitumor or tissue culture activity are recorded in Table VI.
The preparation and reduction of 5‐cyano‐3‐indolylketones. Synthesis of 5‐cyanotryptamines
Authors: Degraw Joseph I. , Kennedy Jill G. , Skinner W. A.
Published: March 2009

The acylation of indoles under acidic conditions has been studied. Stannic chloride was shown to be an effective catalyst for the preparation of some 3‐acylindoles, notably 5‐cyano‐3‐indolylketones. The various 5‐cyano ‐3 ‐ indolylketones were reduced with sodium borohydride to yield either the 5‐cyano‐3‐carbinols or 5‐cyano‐3‐alkylindoles. 5‐Cyanotryptamines were obtained by reduction of appropriate α‐dialkylamino and α‐azidoketones. A cleavage reaction of the carbinols involving loss of the 3‐side chain to yield 5‐cyanoindole is also described.