bluuebunny/crossref_metadata_2025 huggingface dataset:
Depression status as a reliable predictor of functional decline among Japanese community‐dwelling older adults: a 12‐year population‐based prospective cohort study
Authors: Iwasa Hajime , Yoshida Yuko , Kumagai Shu , Ihara Kazushige , Yoshida Hideyo , Suzuki Takao
Published: March 2009

Objective

This study aimed to examine a longitudinal relationship between depression status and functional decline among Japanese community‐dwelling older adults, using a 12‐year population‐based, prospective cohort study design.

Method

A total of 710 men and women, aged 65 years and over, participated in the study. Katz's Index and the Tokyo Metropolitan Institute of Gerontology Index of Competence were used to measure the functional capacities of basic activities of daily living (BADL) and higher‐level competence, respectively. For the purpose of analysis, a decline in each subscale of functional capacity during the follow‐up period were used as outcome variables; depression status assessed by the Japanese version of the 30‐item Geriatric Depression Scale (GDS), with a cut‐off of 11, was used as an independent variable; and age, gender, education level, history of chronic disease, hospitalization, smoking, physical activity, living alone, hearing problems, physical pain, dietary habits, and usual walking speed at baseline were used as covariates.

Results

Use of the multivariate Cox proportional hazards model adjusted for potential confounders showed that depression status was significantly and independently associated with BADL decline (risk ratio (RR) = 1.46, 95% confidence interval (CI): 1.13–1.89) and with higher‐level competence decline (RR = 1.56, 95% CI: 1.18–2.04).

Conclusion

Our study found an independent relationship between depression status and longitudinal change in functional capacity among community‐dwelling older individuals, suggesting that depression status is a reliable predictor of functional decline (both of BADL decline and higher‐level competence decline) in older adults. Copyright © 2009 John Wiley & Sons, Ltd.
Neural cell adhesion molecule expression: No correlation with perineural invasion in cutaneous squamous cell carcinoma of the head and neck
Authors: Solares C. Arturo , Brown Ian , Boyle Glen M. , Parsons Peter G. , Panizza Benedict
Published: March 2009

Background.

Perineural invasion (PNI) in cutaneous squamous cell carcinoma of the head and neck (CSCCHN) is associated with decreased survival, particularly in patients with clinical signs of cranial nerve involvement. There is evidence to indicate that neural cell adhesion molecule (N‐CAM) confers capability of PNI. We analyzed our own patient population to determine if N‐CAM predicted clinical PNI in CSCCHN.

Methods.

Tissue from patients with CSCCHN and clinical PNI, who underwent surgery between 1998 and 2005, was immunostained for N‐CAM. In addition, non‐PNI CSCCHN and normal nerve sections were also stained. A section of neuroendocrine tumor was included in each slide as a positive control. In addition, most of the sections also had an “inbuilt control” in the CD56 positive natural killer T cells that formed part of the inflammatory reaction to the tumors.

Results.

Tissue was available from 14 patients with CSCCHN and clinical PNI. The analysis was carried out in 14 patients without PNI and 4 normal nerves. N‐CAM was not expressed in any of our PNI CSCCHN specimens or non‐PNI controls. It was strongly expressed in the neuroendocrine tumors and positive in‐built controls, as well as in normal nerve tissue.

Conclusion.

N‐CAM expression did not predict neurotropism in our patient population. Additional studies are required to identify the cell surface markers expressed by CSCCHN which confer neurotropism capabilities. © 2009 Wiley Periodicals, Inc. Head Neck, 2009
A new, simple maxillary‐sparing tongue depressor for external mandibular radiotherapy: A case report
Authors: Bodard Anne‐Gaëlle , Racadot Séverine , Salino Samuel , Pommier Pascal , Zrounba Philippe , Montbarbon Xavier
Published: March 2009

Background.

In external radiotherapy, the use of leaded intraoral devices to shield adjacent tissues is well described, but stabilization of the mandible is often realized with standard bite blocks, which do not allow a good stabilization of the mandible.

Methods and Results.

A 40‐year‐old patient presenting with a local recurrence of a tumor of the floor of the mouth underwent external radiotherapy. To shield the maxilla during mandibular irradiation and to ensure mandible and tongue immobility during external radiotherapy, a custom‐made device was realized. The apparatus consists of a polymethylmethacrylate resin plate and 2 wedges. Only 2 steps are needed.

Conclusion.

The realization is simple and cheap, the apparatus is comfortable, and modifications are easy. It can be used in all patients, except in patients with totally mandibular edentulous with severe bone resorption. © 2009 Wiley Periodicals, Inc. Head Neck, 2009
Prognostic factors for the malignant triton tumor of the head and neck
Authors: Terzic Andrej , Bode Beata , Gratz Klaus W. , Stoeckli Sandro J.
Published: March 2009

Background.

Malignant triton tumors are rare neoplasias consisting of a malignant peripheral nerve sheath tumor with additional rhabdomyoblastic differentiation. These tumors are highly aggressive and prognosis is poor. Our aim is to describe the outcome and to identify potential prognostic factors.

Methods.

From 1993 to 2005, 7 patients with a malignant triton tumor of the head and neck were treated at our institution. A literature search revealed another 46 published cases. All these cases were analyzed for outcome and prognostic factors.

Results.

Patients with primary tumors involving the nose and paranasal sinuses have better, patients involving the neck a poor prognosis. All other locations show an intermediate course. Complete surgical removal is of crucial importance. Additional radiation or chemotherapy show little effect.

Conclusion.

Location of the primary tumor is a key factor for prognosis. Complete surgical removal is the only treatment associated with survival.© 2009 Wiley Periodicals, Inc. Head Neck, 2009
Larynx preservation clinical trial design: Key issues and recommendations—A consensus panel summary
Authors: Lefebvre Jean‐Louis , Ang K. Kian ,   on behalf of the Larynx Preservation Consensus Panel
Published: March 2009

Background

To develop guidelines for the conduct of phase III clinical trials of larynx preservation in patients with locally advanced laryngeal and hypopharyngeal cancer.

Methods

A multidisciplinary international consensus panel developed recommendations after reviewing results from completed phase III randomized trials, meta‐analyses, and published clinical reports with updates available through November 2007. The guidelines were reviewed and approved by the panel.

Results

The trial population should include patients with T2 or T3 laryngeal or hypopharyngeal squamous cell carcinoma not considered for partial laryngectomy and exclude those with laryngeal dysfunction or age more than 70 years. Functional assessments should include speech and swallowing. Voice should be routinely assessed with a simple, validated instrument. The primary endpoint should capture survival and function. The panel created a new endpoint: laryngo‐esophageal dysfunction‐free survival. Events are death, local relapse, total or partial laryngectomy, tracheotomy at 2 years or later, or feeding tube at 2 years or later. Recommended secondary endpoints are overall survival, progression‐free survival, locoregional control, time to tracheotomy, time to laryngectomy, time to discontinuation of feeding tube, and quality of life/patient reported outcomes. Correlative biomarker studies for near‐term trials should include EGFR, ERCC‐1, E‐cadherin and β‐catenin, epiregulin and amphiregulin, and TP53 mutation.

Conclusions

Revised trial designs in several key areas are needed to advance the study of larynx preservation. With consistent methodologies, clinical trials can more effectively evaluate and quantify the therapeutic benefit of novel treatment options for patients with locally‐advanced laryngeal and hypopharyngeal cancer. © 2009 Wiley Periodicals, Inc. Head Neck, 2009
The older‐worker‐younger‐supervisor dyad: A test of the Reverse Pygmalion effect
Authors: Collins Mary Hair , Hair, Jr. Joseph F. , Rocco Tonette S.
Published: March 2009

An emerging phenomenon, the older worker reporting to a much younger supervisor, is reversing the tradition that managers are older and more experienced than subordinates. These age‐related demographic changes are bringing about a role reversal in the workplace that violates established age norms, creating status incongruence in the supervisor‐subordinate dyad. This age‐reversed dyad can be better understood by examining generational differences and the effects of older workers' expectations on their younger supervisors' leadership behavior, referred to as Reverse Pygmalion. Research findings highlight demographic differences and similarities in the supervisor‐subordinate dyad, called Relational Demography. Major findings are that older workers expect less from their younger supervisors than do younger workers, and in turn older workers rate their younger supervisors' leadership behavior lower than younger workers rate their younger supervisors.
The coach‐coachee relationship in executive coaching: A field study
Authors: Baron Louis , Morin Lucie
Published: March 2009

Numerous authors have suggested that the working relationship between coach and coachee constitutes an essential condition to the success of executive coaching. This study empirically investigated the links between the coach‐coachee relationship and the success of a coaching intervention in an organizational setting. Data were collected from two samples: 73 managers who received executive coaching for a period of eight months and 24 coaches. Results from 31 coach‐coachee dyads were analyzed. Results indicate that the coach‐coachee relationship plays a mediating role between the coaching received and development of the coachees' self‐efficacy. Findings also show four significant correlates to the coach‐coachee relationship: the coach's self‐efficacy with regard to facilitating learning and results, the coachee's motivation to transfer, his or her perception of supervisor support, and the number of coaching sessions received.
Ziprasidone as an adjuvant for clozapine‐ or olanzapine‐associated medical morbidity in chronic schizophrenia
Authors: Henderson David C. , Fan Xiaoduo , Copeland Paul M. , Sharma Bikash , Borba Christina P. , Forstbauer Sharon I. , Miley Kate , Boxill Ryan , Freudenreich Oliver , Cather Corrine , Evins Anne E. , Goff Donald C.
Published: March 2009

Objective

This study sought to examine the effect of ziprasidone on olanzapine or clozapine‐associated medical morbidity such as insulin resistance, diabetes mellitus (DM) and impaired fasting glucose, obesity, and hyperlipidemia in patients with schizophrenia or schizoaffective disorder.

Method

This was a 6‐week, open label trial of ziprasidone 160 mg/day added to a stable dose of olanzapine or clozapine in 21 schizophrenia or schizoaffective patients with DM, impaired fasting glucose, or insulin resistance.

Results

Ten olanzapine‐treated subjects and 11 clozapine‐treated subjects were enrolled in the study. There were no significant differences between the two groups at baseline for age, gender, education, ethnicity, BMI, cholesterol levels, or fasting glucose. At week 6, there were no significant changes in weight, BMI, cholesterol levels, or fasting glucose. There was no significant difference in psychotic, negative, or depressive symptoms. QTc significantly increased at week 2 but not at week 6.

Conclusions

The addition of 160 mg/day of ziprasidone was well tolerated but did not produce significant improvement in fasting glucose, insulin resistance, hyperlipidemia or lead to weight loss in olanzapine‐ or clozapine‐treated subjects with schizophrenia or schizoaffective disorder. Copyright © 2009 John Wiley & Sons, Ltd.
A study of soil water movement combining soil water potential with stable isotopes at two sites of shallow groundwater areas in the North China Plain
Authors: Song Xianfang , Wang Shiqin , Xiao Guoqiang , Wang Zhimin , Liu Xin , Wang Peng
Published: March 2009

In the shallow groundwater areas of the North China Plain (NCP), precipitation infiltration and evapotranspiration in the vertical direction are the main processes of the water cycle, in which the unsaturated zone plays an important role in the transformation process between precipitation and groundwater. In this paper, two typical sites in Cangzhou (CZ) and Hengshui (HS) of Hebei province with shallow water tables were selected to analyse the relationship among precipitation, soil water and groundwater. At each site, precipitation, soil water at depths 10, 20, 30, 50, 70, 100, 150, 200, 300 cm, and groundwater were sampled to analyse the stable isotope compositions of hydrogen and oxygen. The soil water potentials at the corresponding depths were observed. Although the climates at the two sites are similar, there are some differences in the infiltration process, soil water movement and groundwater recharge sources. Evaporation occurred at the upper depths, which led to the decrease of soil potential and the enrichment of heavy isotopes. At the CZ site, precipitation infiltrated with piston mode, and an obvious mixture effect existed during the infiltration process. Preferential flow may exist in the soil above 100 cm depth. However, at the HS site soil water moved in piston mode, and groundwater was mainly recharged by precipitation. When precipitation recharged the groundwater it experienced a strong evaporation effect. The results of the soil water movement mechanism provides the transformation relationship among precipitation, soil water and groundwater in the middle and eastern NCP. Copyright © 2009 John Wiley & Sons, Ltd.
A comparative Raman and CARS imaging study of colon tissue
Authors: Krafft Christoph , Ramoji Anuradha A. , Bielecki Christiane , Vogler Nadine , Meyer Tobias , Akimov Denis , Rösch Petra , Schmitt Michael , Dietzek Benjamin , Petersen Iver , Stallmach Andreas , Popp Jürgen
Published: March 2009

An experimental evaluation of the information content of two complimentary techniques, linear Raman and coherent anti‐Stokes Raman scattering (CARS) microscopy, is presented. CARS is a nonlinear variant of Raman spectroscopy that enables rapid acquisition of images within seconds in combination with laser scanning microscopes. CARS images were recorded from thin colon tissue sections at 2850, 1660, 1450 and 1000 cm–1 and compared with Raman images. Raman images were obtained from univariate and multivariate (k‐means clustering) methods, whereas all CARS images represent univariate results. Variances within tissue sections could be visualized in chemical maps of CARS and Raman images. However, identification of tissue types and characterization of variances between different tissue sections were only possible by analysis of cluster mean spectra, obtained from k‐means cluster analysis. This first comparison establishes the foundation for further development of the CARS technology to assess tissue. (© 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim)
Collagen scaffolds loaded with collagen‐binding NGF‐β accelerate ulcer healing
Authors: Sun Wenjie , Lin Hang , Chen Bing , Zhao Wenxue , Zhao Yannan , Xiao Zhifeng , Dai Jianwu
Published: March 2009

Studies have shown that exogenous nerve growth factor (NGF) accelerates ulcer healing, but the inefficient growth factor delivery system limits its clinical application. In this report, we found that the native human NGF‐β fused with a collagen‐binding domain (CBD) could form a collagen‐based NGF targeting delivery system, and the CBD‐fused NGF‐β could bind to collagen membranes efficiently. Using the rabbit dermal ischemic ulcer model, we have found that this targeting delivery system maintains a higher concentration and stronger bioactivity of NGF‐β on the collagen membranes by promoting peripheral nerve growth. Furthermore, it enhances the rate of ulcer healing through accelerating the re‐epithelialization of dermal ulcer wounds and the formation of capillary lumens within the newly formed tissue area. Thus, collagen membranes loaded with collagen‐targeting human NGF‐β accelerate ulcer healing efficiently. © 2009 Wiley Periodicals, Inc. J Biomed Mater Res, 2010
Effects of hydrostatic pressure on leporine meniscus cell‐seeded PLLA scaffolds
Authors: Gunja Najmuddin J. , Athanasiou Kyriacos A.
Published: March 2009

Hydrostatic pressure (HP) is an important component of the loading environment of the knee joint. Studies with articular chondrocytes and TMJ disc fibrochondrocytes have identified certain benefits of HP for tissue engineering purposes. However, similar studies with meniscus cells are lacking. Thus, in this experiment, the effects of applying 10 MPa of HP at three different frequencies (0, 0.1, and 1 Hz) to leporine meniscus cell‐seeded PLLA scaffolds were examined. HP was applied once every 3 days for 1 h for a period of 28 days. Constructs were analyzed for cellular, biochemical, and biomechanical properties. At t = 4 weeks, total collagen/scaffold was found to be significantly higher in the 10 MPa, 0 Hz group when compared with other groups. This despite the fact that the cell numbers/scaffold were found to be lower in all HP groups when compared with the culture control. Additionally, the total GAG/scaffold, instantaneous modulus, and relaxation modulus were significantly increased in the 10 MPa, 0 Hz group when compared with the culture control. In summary, this experiment provides evidence for the benefit of a 10 MPa, 0 Hz stimulus, on both biochemical and biomechanical aspects, for the purposes of meniscus tissue engineering using PLLA scaffolds. © 2009 Wiley Periodicals, Inc. J Biomed Mater Res, 2010
Problems related to the synthesis of 3‐aziridinyl‐6‐chloropyridazine
Authors: Nyberg Wayne H. , Cheng C. C.
Published: March 2009

The correct structure of the reported 3‐aziridinyl‐6‐chloropyridazine was found to be 3‐[β‐(1‐aziridinyl)ethylamino]‐6‐chloropyridazine, which was confirmed by n. m. r. studies. The relative ease of nucleophilic displacement of a methylsulfonyl group versus a chloro group in equivalent positions on a pyridazine or a pyrimidine ring was compared. It was observed that the chloro rather than the methylsulfonyl group was preferentially replaced, as illustrated by substitution studies of 3‐chloro‐6‐methylsulfonylpyridazine and 4‐chloro‐6‐methylsulfonylpyrimidine.
The synthesis of imidazo[4,5‐c]‐, s‐triazolo[4,3‐b]‐, and tetrazolo[1,5‐b]pyridazines
Authors: Kuraishi Tsukasa , Castle Raymond N.
Published: March 2009

The adenine analog, 7‐aminoimidazo[4,5‐c]pyridazine (XII) and three other members of this previously unknown ring system have been prepared. The adenine analog, 8‐amino‐tetrazolo[1,5‐b]pyridazine (I) has also been prepared together with three other compounds in this ring system. The novel displacement of halogen in nitrogen heterocycles with phosphorus pentasulfide has been extended.
Reisert compound studies. VI. The condensation of aldehydes with 2‐benzoyl‐1,2‐dihydroisoquinaldonitrile
Authors: Popp Frank D. , Gibson Harry W.
Published: March 2009

In 1958 McEwan and coworkers (4) reported the condensation of the lithium salts of 1‐benzoyl‐1,2‐dihydroquinaldonitrile and 2‐benzoyl‐1,2‐dihydroiso‐quinaldonitrile (I) with aldehydes to form esters of secondary alcohols containing the 2‐quinoyl or 1‐iso‐quinoyl (II) group bonded to the carbinol carbon atom. This method was used to devise from appropriate Reissert compounds a convenient synthesis of papaverinol (5) and some attractive intermediates for eventual conversion to the ipecac alkaloids (6).
The synthesis of 9‐acridanylmethyl and 9‐acridinylmethyl ketones
Authors: Sheppard Chester S. , Levine Robert
Published: March 2009

A series of new 9‐acridanylmethyl ketones has been prepared by the 9, 10‐addition of the sodium derivatives of a number of ketones to acridine. The 9‐acridanylmethyl ketones were dehydrogenated to the corresponding 9‐acridinylmethyl ketones by either acidic ferric chloride or lead tetraacetate. A route of more limited utility for the synthesis of 9‐acridinylmethyl ketones involves the acylation of 9‐acridinylmethyllithium with certain esters. The attempted ketonic cleavage of α‐(9‐acridinyl)‐β‐ketoesters such as ethyl α‐(9‐acridinyl)isonicotinoylacetate and ethyl α‐(9‐acridinyl)benzoylacetate is an unsatisfactory method for obtaining the corresponding 9‐acridinylmethyl ketones since these ketones are cleaved to 9‐methylacridine under mildly acidic or basic conditions.
2,2′‐P‐phenylenebis(4‐methyl‐5‐phenyloxazole) and other solutes for scintillation counting
Authors: Walker Derek , Waugh Thomas D.
Published: March 2009

The advent of large liquid scintillation counters has created a need for a secondary solute which is more soluble in organic solvents than is 2,2′‐p‐phenylenebis(5‐phenyl‐oxazole) (POPOP, I or II, R‐substituents = H), the preferred secondary solute for small‐scale work.
The stereochemistry of some dihydro‐1,3‐oxazine derivatives
Authors: Chylińska J. B. , Urbański T.
Published: March 2009

The conformations of one dihydro‐1,3‐benzoxazine and two dihydro‐1,3‐naphthoxazines were studied by calculating and measuring their dipole moments.

A “semi‐chair” form with a quasi‐axial position of the N‐substituent was found to be most probable.
6‐Substituted acridizinium derivatives
Authors: Bradsher C. K. , Parham J. C.
Published: March 2009

Through quaternization of an acetal of picolinaldehyde with suitable α‐haloalkylarenes, a number of acridizinium salts, having a substituent at the meso position adjacent to nitrogen, have been prepared. Similarly, the ketal derived from α‐acetopyridine has been used to prepare the first acridizinium derivatives having methyl groups at both of the meso positions.
Pyrimidines. XIII. 2‐ and 6‐substituted 4‐pyrimidinecarboxylic acids
Authors: Daves G. Doyle , O'Brien Darrell E. , Lewis Leland R. , Cheng C. C.
Published: March 2009

The “abnormal” behavior of 4,6‐dimethyl‐2‐pyrimidinol towards nitrous acid has been clarified. The reaction between 4‐methyl‐2‐pyrimidinol and nitrous acid has been utilized as a new synthetic procedure for the preparation of several 2‐substituted 4‐pyrimidinecarboxylic acids. 2‐Hydroxy‐4‐pyrimidinecarboxylic acid has also been prepared from 4‐chloro‐2‐methylthiopyrimidine via the trimethylammonium intermediate. 6‐Amino‐ and 6‐thio‐4‐pyrimidinecarboxylic acids have been readily prepared from the previously reported 6‐hydroxy‐4‐pyrimidinecarboxylic acid.
The chemistry of triazine derivatives II. The acylation of 2,4,6‐trimethyl‐s‐triazine to triazinyl ketones and their facile isomerization to acetamidopyrimidines
Authors: Osborne David R. , Wieder William T. , Levine Robert
Published: March 2009

A series of triazinyl ketones has been prepared by acylating 2,4,6‐trialkyl‐s‐triazines and these ketones have been isomerized to 4‐acylamidopyrimidine derivatives. A possible mechanism for this isomerization is suggested.
A novel ring closure of 1‐acyl‐2,2‐dialkylhydrazines
Authors: Meyer Robert F. , Cummings Betty L.
Published: March 2009

A series of 14 new 2; 4‐substituted‐δ2‐1, 3, 4‐oxadiazolin‐5‐ones was prepared by a novel ring closure of the corresponding l‐acyl‐2, 2‐dialkylhydrazines with phosgene, whereby one alkyl group is lost as alkyl chloride. This new cyclization was carried out too with thiophosgene and with p‐chlorothiobenzoic acid, 2, 2‐dimethylhydrazide to give the corresponding 2,4‐disubstituted‐δ2‐1, 3, 4‐oxadiazoline‐5‐thione, ‐thiadiazolin‐5‐one and ‐thiadiazoline‐5‐thione, respectively.
Cinnoline chemistry X. The infrared spectra of halogen substituted 4‐hydroxy‐ and 4‐mercaptocinnolines
Authors: Shoup Regitze R. , Castle Raymond N.
Published: March 2009

The infrared spectra of a series of 4‐hydroxy‐ and 4‐mercaptocinnolines substituted with fluorine, chlorine or bromine in the 5‐, 6‐, 7‐ and 8‐position have been obtained in potassium bromide discs between 4000 and 400 cm−1. Assignments for most of these bands have been made.
Synthesis of 1‐methyl‐3H‐1,4‐benzodiazepline‐2,5 (1H,4H) ‐dione and derivatives
Authors: Lee Cheuk‐Man
Published: March 2009

Derivatives of l‐methyl‐3H‐1, 4‐benzodiazepine‐2,5(1H, 4H)‐dione were synthesized by ring closure of substituted 2[(N‐chloroacetyl‐N‐methyl)amino]benzamides with sodium methoxide in methanol.
Indazole‐3‐carboxylic acids and their derivatives
Authors: Buu‐Hoi N. P. , Hoeffinger J. P. , Jacquignon P.
Published: March 2009

The preparation of indazole‐3‐carboxylic acids from the appropriate isatins by von Auwers' method has been investigated; these acids were used for acceding to the corresponding indazoles and for preparing hydrazides and hydrazones in the indazole series.
Hydrogenation of 3‐(2‐nitrobenzoyl) ‐2‐benzoxazolinone to 1‐hydroxy‐3‐ (2‐hydroxyphenyl) quinazoline‐2,4‐dione
Authors: Sam Joseph , Richmond C. W.
Published: March 2009

The preparations of the compounds noted in the title are described. The reduction of l‐hydroxy‐3‐(2‐hydroxyphenyl)quinazoline‐2, 4‐dione (III) catalyzed by Raney nickel provided 3‐(2‐hydroxyphenyl)quinazoline‐2, 4‐dione (VI).
The synthesis of v‐triazolo[4,5‐c]pyridazines, a new heterocyclic ring system as potential purine antagonists
Authors: Gerhardt G. Anne , Castle Raymond N.
Published: March 2009

The free ring system, v‐triazolo[4, 5‐clpyridazine and several derivatives in this ring system such as the adenine analog, 7‐amino‐v‐triazolo[4, 5‐clpyridazine, have been prepared. In addition, the fully aromatic pyrazino[2, 3‐clpyridazine ring system has been prepared for the first time.
Reissert compound studies. VII. The synthesis of calycotomine
Authors: Gibson Harry W. , Popp Frank D. , Catala Adria
Published: March 2009

The alkaloid calycotomine has been synthesized in 44% overall yield by use of the Reissert compound of 6, 7‐dimethoxyisoquinoline.
Organic fluoronitrogens. I. The direct fluorination of melon
Authors: Erickson John G. , Brown Harvey A. , Husted Donald R.
Published: March 2009

The action of elemental fluorine upon the complex polyheterocycle, melon, yields products which contain 50% or more of fluorine and are solids or liquids of very low volatility. The structure assigned indicates essential retention of the tri‐s‐triazine structure, with addition of fluorine to most of the double bonds, replacement of hydrogen by fluorine, and a minor amount of cleavage of carbon‐nitrogen bonds.
Pyrimidines. XIV. Synthesis of 1‐substituted 5,6‐dihydrocytosines and an improved synthesis of 1‐substituted uracils
Authors: Cheng C. C. , Lewis Leland R.
Published: March 2009

1‐Substituted 5, 6‐dihydrouracils (VI) and 1‐substituted 5, 6‐dihydrocytosines (V) were prepared by cyclization of N‐substituted N‐β‐cyanoethyl ureas (IV) in acid and basic medium, respectively. Compounds N were synthesized from cyanic acid and β‐(substituted amino)propionitriles (III), the latter in turn were prepared from primary amines (I) and acrylonitrile (II).

Preparations of 1‐substituted uracils (VII) from VI were carried out by known procedures.
Synthesis of 1‐hydroxyxanthines
Authors: Bauer Ludwig , Nambury C. N. V. , Dhawan Devindra
Published: March 2009

The synthesis of 1‐hydroxy‐7‐alkylxanthines from the corresponding diethyl 1‐alkyl‐4,5‐imidazoledicarboxylates by means of a modified Lossen rearrangement is described. The products were characterized by their spectra and identified by hydrolysis with concentrated hydrochloric acid at elevated temperatures to the corresponding N‐alkyl‐substituted glycines.
Nuclear magnetic resonance spectral analyses of isothiazoles
Authors: Anderson Richard C.
Published: March 2009

N.m.r. spectral analyses of isothiazole and its methyl homologs permits assignment of chemical shifts and coupling constants for each of the protons in these molecules. The chemical shift values for hydrogens attached to the isothiazole nucleus substantiate electron density values calculated from molecular orbital theory. In 5‐methylisothiazole, the coupling constant for the hydrogen atom at position 3 and those on the methyl group is larger than for hydrogens attached directly to the isothiazole nucleus at positions 3 and 5.
The synthesis of steroidal 16α,17α‐fused isoxazolines and isoxazolidines
Authors: Culbertson T. P. , Moersch G. W. , Neuklis W. A.
Published: March 2009

The reaction of nitrile oxides with Δ16‐steroids substituted at C‐17 by COCH3, OCOCH3, CN, NHCOCH3 and H afforded 16α, 17α‐[3, 1‐(2‐isoxazolino)]‐steroids. From the reaction of C,N‐diphenylnitrone with pregna‐5,16‐diene‐3β‐ol‐20‐one acetate two isomeric products were isolated, 16α, 17α‐(2, 3‐diphenyl‐3,1‐isoxazolidino)‐pregn‐5‐en‐3β‐ol‐20‐one acetate and 16α, 17α ‐ (2, 3 ‐diphenyl ‐ 1, 3 ‐isoxazolidino)‐pregn‐5‐en‐3β‐01‐20‐one acetate.
Pyridazines. II. The synthesis of amino‐, azido‐ and nitraminopyridazines, tetrazolo[1,5‐b] pyridazines and related nitrogen heterocycles
Authors: Guither William D. , Clark Donald G. , Castle Raymond N.
Published: March 2009

The remaining three diaminopyridazines, 3, 4, 5‐triaminopyridazine and several nitraminopyridazines have been prepared. The structure of 3,4, 5‐triaminopyridazine and the 3, 5‐diamino‐4‐nitropyridazine precursor have been established by n.in.r. analysis. In addition 8‐amino‐6‐chloro‐, 8‐amino‐6‐hydrazino‐ and 8‐amino‐6‐azidotetrazolo‐[1, 5‐b]pyridazine has been synthesized along with 4, 6‐dihydrazino‐ and 4, 6‐diazido‐pyrimidine. Several other chemical transformation of these compounds are described.
The alkylation of 6‐aryl‐6,7‐diazaspiro [3.4]octane‐5,8‐diones
Authors: Brabander Herbert J. , Wright William B.
Published: March 2009

The synthesis of 8‐tert‐aminoalkoxy‐6‐aryl‐6,7‐diazaspiro[3.4]oct‐7‐en‐5‐ones (1) and 6‐tert‐aminoalkyl‐7‐aryl‐6,7‐diazaspiro[3.4]octane‐5,8‐diones has been accomplished. Two synthetic methods are described, each of which yields principally one isomer or the other.
Difluorodiazirine. V. difluoromethyl esters and ethers
Authors: Mitsch Ronald A. , Robertson Jerry E.
Published: March 2009

The preparation of difluoromethyl esters and ethers by the photolytic reaction of difluorodiazirine with acids and alcohols, respectively, is described. Difluoromethyl benzoate is converted, under mild conditions, to methyl benzoate, benzamide and benzanilide by reaction with methanol, ammonium hydroxide and aniline, respectively. The difluoromethyl esters are activated to nucleophilic reaction by virtue of the α‐fluorine substitution.
Analogs of tetrahydrofolic acid. XXVI. synthesis of some 5‐aryl and 5‐aralkyl pyrimidine‐6‐carboxylic acids and their effect on dihydrofolic reductase and thymidylate synthetase
Authors: Baker B. R. , Jordaan Johannes H.
Published: March 2009

2‐Amino‐4‐hydroxy‐5‐(4‐phenylbutyl)pyrimidine‐6‐carboxylic acid (V) was synthesized from isopropyl 2‐ethoxalyl‐6‐phenylhexanoate (XIII) by conversion to acyl guanide (XV) with guanidine followed by anhydrous acid catalyzed ring closure to ethyl 2‐amino‐α‐(4‐phenylbutyl)‐4‐oxo‐2‐imidazoline‐Δ5,α‐acetate (XXIII) and base catalyzed rearrangement to V; similarly, p‐chlorophenylacetonitrile was converted to 5‐(p‐chlorophenyl)‐2,4‐diaminopyrimidine‐6‐carboxylic acid (VIII). Claisen condensation of isopropyl 6‐phenylhexanoate (XI) or p‐chlorophenylacetonitrile with ethyl trifluoroacetate followed by condensation with guanidine afforded 2‐amino‐5‐(4‐phenylbutyl)‐6‐(trifluoromethyl)‐4‐pyrimidinol (XXVI) and 5 ‐ (p‐chlorophenyl) ‐2,4 ‐diamino‐6‐(trifluoromethyl)pyrimidine (XXXIV). Evaluation of V, VIII, XXVI, and XXXIV as inhibitors of dihydrofolic reductase showed that the 6‐carboxyl, 6‐trifluoromethyl, and 6‐carbethoxy groups greatly reduced the effectiveness as inhibitors of dihydrofolic reductase compared to the corresponding 6‐methyl derivatives. The inhibition data appear to make unlikely the possibility of the pyrimidines binding to the enzyme by four hydrogen bonds as propounded by Zakrzewski (19) or by binding through a charge‐transfer complex, but supports the concept (18) of an anionic‐cationic interaction for the protonated 2,4‐diaminopyrimidines; a weak base ‐weak acid interaction for a non‐protonated pyrimidine that is stronger than a hydrogen bond is also proposed.
Liquid scintillators. XIII. steric inhibition of resonance in liquid scintillators
Authors: Taber Richard L. , Daub Guido H. , Hayes F. Newton , Ott Donald G.
Published: March 2009

2″,3′ ‐ Dimethyl ‐ p ‐ quaterphenyl (I), 2″, 3′, 5′, 6″ ‐tetramethyl ‐ p ‐ quaterphenyl (II), 6,7 ‐ dihydro ‐ 6 ‐ methyl ‐ 3, 9 ‐ diphenyl ‐ 5H ‐ dibenz[c,e]azepine (III), 5,7 ‐ dihydro ‐ 3, 9 ‐ diphenyl ‐ dibenzo[c,e]thiepin (IV), 5,7 ‐ dihydro ‐ 3,9 ‐ diphenyldibenzo[c,e]selenepin (V), and 6, 6 ‐ dicarbethoxy ‐ 6,7 ‐ dihydro ‐ 3,9 ‐ diphenyl ‐ 5H ‐ dibenzo[a,c]cycloheptene (VI) have been synthesized and screened as potential primary liquid scintillation solutes. The scintil‐ lation properties of I, II, III, IV, V, and VI have been compared with 2,7‐diphenyl‐ fluorene (VII) (4), 9,10‐dihydro‐2,7‐diphenylphenanthrene (VIII) (5), and 5,7‐dihydro‐ 3, 9‐diphenyldibenz[c,e]oxepin (IX) (5). The relative pulse‐heights of I, VI, VII, VIII, and IX at 3 mM in toluene gave a linear relationship when plotted against the cos2 of the respective estimated angles of torsion about the 1″. 4′‐bond in the p‐quaterphenyl system. The azepine III, thiepin IV, selenepin V, and tetramethyl‐p‐quaterphenyl II were very poor scintillators in toluene solution.
Pyrazolo [3,4‐b]pyridines and pyrazolo[3′,4′:6,5]pyrido[2,3‐d]pyrimidines
Authors: Cottis Steve G. , Clarke Priscilla B. , Tieckelmann Howard
Published: March 2009

3,6‐Diamino‐5‐cyanopyrazolo[3,4‐b]pyridine (III) and 1‐methyl‐3, 6‐diamino‐5‐cyanopyrazolo[3,4‐b]pyridine (IV) were formed by treatment of 2‐amino‐6‐chloro‐3, 5‐dicyanopyridine with hydrazine and methylhydrazine. Pyrazolo[3′,4′:6,5]pyrido[2,3‐d]pyrimidines were formed from IV and from a number of its derivatives.
Acridizinium betaines
Authors: Bradsher C. K. , Parham J. C. , Turner J. D.
Published: March 2009

The quaternary salts formed by reaction of tolyl sultone (2, 1, 3H‐benzoxathiole‐1, 1‐dioxide) with 2‐(1,3‐dioxolan‐2‐yl)‐ or 2‐(2‐methyl[1, 3]dioxolan‐2‐yl)pyridine may be cyclized in acid to afford the betaines derived from 7‐sulfo‐ and 7‐sulfo‐11‐methylacridizinium hydroxides. Similarly 1‐(1,3‐dioxolan‐2‐yl)isoquinoline may be converted to the betaine of 9‐sulfobenzo[a]acridizinium hydroxide.

The sodium salt of 2‐(3′‐sulfobenzoyl)pyridine may be quaternized with benzyl bromide and the resulting betaine cgclized to afford the betaine of 11‐(3′‐sulfophenyl)acridizinium hydroxide.
Benzo[b]thiophene derivatives. VII. An abnormal substitution product from 3‐chloromethylbenzo[b]thiophene
Authors: Campaigne E. , Neiss E. S.
Published: March 2009

The alkylation of cyanide ion with 3‐chloromethylbenzo[b]thiophene gave a higher yield of benzo[b]thiophene‐3‐acetonitrile in dimethyl sulfoxide than in alcohol, and in addition 2‐cyano‐3‐methylbenzo[b]thiophene was obtained as a by‐product in this solvent. The abnormal product was prepared by an alternative, unequivocal synthesis. The isomers were hydrolyzed to their respective acids, which were reduced to 3+(β‐hydroxyethyl)benzo[b]thiophene and 2‐hydroxymethyl‐3‐methylbenzo[b]thiophene. The ultraviolet and nuclear magnetic resonance spectra of these compounds are reported.
Imidazo[4,5‐d]pyridazines. IV. Synthesis of 4,7 disubstituted derivatives and 1‐benzyl‐2‐substituted thio derivatives
Authors: Gerhardt G. Anne , Aldous Duane L. , Castle Raymond N.
Published: March 2009

Seventy‐five new imidazo[4,5‐d]pyridazines and three new imidazoles have been prepared for antitumor testing. Antitumor screening results are reported for thirty‐five of these compounds. No significant activity was observed.
The mass spectra of oxygen heterocycles I. The 4‐hydroxy‐3‐phenylcoumarins (isoflavonols)
Authors: Pelter A. , Stainton P. , Johnson A. P. , Barber M.
Published: March 2009

The unique breakdown patterns of the 4‐hydroxy‐3‐phenylcoumarins (isoflavonols) in the mass spectrometer have been examined. Explanations of the fragmentations found have been confirmed by deuteration studies and by an examination of the mass spectra of 4‐methoxy‐3 ‐phenylcoumarins. The scheme has been extended 4 to 7‐dihydroxycoumarin, which is contrasted with 4‐methyl.‐7‐hydroxycoumarin.
The mass spectra of oxygen heterocycles. II. The mass spectra of some flavonoids
Authors: Pelter Andrew , Stainton P. , Barber M.
Published: March 2009

The mass spectra of the flavones apigenin and acacetin have been reported by Wilson and Reed (1) whilst the mass spectrum of flavone itself has been described by Barnes and Occolowitz (2). A discrepancy between the results obtained lies in the importance assumed by breakdown via a Diels‐Alder reaction (described as mode A in paper I (3) of this series) in the natural products as compared with the parent compound.
Morphanthridines I. 11‐aminoalkylidene‐and ll‐(4‐Piperidylene)‐5,6‐dihydromorphanthridines
Authors: Drukker Alexander E. , Judd Claude I. , Spoerl Joan M. , Kaminski Frank E.
Published: March 2009

New methods are described for the preparation of 5,6‐dihydro‐11‐morphanthridone, 5‐substituted 5,6‐dihydro‐11‐morphanthridones and nuclear halogenated derivatives. Basic Grignard reagents convert these ketones to carbinols, which through dehydration affords a convenient route to straight chain and cyclic 11‐aminoalkylidene derivatives.
Synthesis of fused imidazo‐heterocyclic systems
Authors: Werbel Leslie M. , Zamora Maria L.
Published: March 2009

The reaction of phenylacyl bromide and a variety of α‐aminoheterocycles was investigated to determine its applicability to the preparation of fused imidazo‐heterocyclic systems. The imidazo[1, 2‐a]pyrazine, imidazo[1, 2‐b]pyridazine, and imidazo[1,2‐a]‐benzimidazole systems and some variations of the imidazo[1,2‐a]pyridine, imidazo[2,1‐b]‐thiazole, imidazotriazine, imidazo[2,1‐b]‐1,3,4‐thiadiazole systems are described.
Cyclizations of 3,4,5‐triamino‐s‐triazole (guanazine) and 3,4‐diamino‐5‐mercapto‐s‐triazole with acetic anhydride
Authors: Child Ralph G. , Tomcufcik Andrew S.
Published: March 2009

Cyclizations of either guanazine (I) or 3,4‐diamino‐5‐mercapto‐s‐triazole (VI) with acetic anhydride leads to 3‐amino‐6‐methyl‐s‐triazolo[4,3‐b]‐s‐triazole and 5‐amino‐2‐methyl‐s‐triazolo[3,4‐b]‐1, 3,4‐thiadiazole, respectively, as well as their acetyl derivatives.
Imidazo [1,2‐a] pyridinium salts
Authors: Bradsher C. K. , Litzinger E. F. , Zinn M. F.
Published: March 2009

2‐Alkylamino‐ or arylaminopyridines react directly with α‐bromoketones to afford 1‐alkyl‐ or 1‐arylimidazo[1,2‐a]pyridinium salts with substituents at position 2. Use of chloroacetaldoxime as the quaternizing agent yields (after hydrolysis) the imidazo‐[1,2‐a]pyridinium ion with no substituent at position 2. The earlier supposition that alkylation of imidazo[1,2‐a]pyridines occurs in position 1 has been shown to be correct.

It has been pointed out that the 1‐substituted imidazo[1, 2‐a]pyridinium system is but one of a group of aromatic heterocyclic systems isoelectronic with the quinolizinium system.
Synthesis of cis,cis‐4,8‐dimethyl‐cis‐2,6‐dioxadecahydroazulene
Authors: Krapcho A. Paul , Mundy Bradford P.
Published: March 2009

In the course of investigating the preparation of a cis‐decahydroazulene (bicyclo‐[5.3.0]decane) ring system, a dioxa analog was synthesized as a model compound. This paper describes the preparation of the hitherto unknown heterocyclic system cis,cis‐4, 8‐dimethyl‐cis‐2, 6‐dioxadecahydroazulene (IX).
Azasteroids II. Approaches to the 13‐azaequilenin system
Authors: Schleigh William R. , Catala Adria , Popp Frank D.
Published: March 2009

The synthesis of N‐[2‐(1‐naphthyl)ethyl]succinimide, N‐[2‐(1‐naphthyl)ethyl]pyrrolidone and the corresponding 3,4‐dihydro compounds is described. The pyrrolidones have been converted into 11,12,16,17‐tetrahydro‐13‐azacyclopenta[a]phenanthrene and 6,7,11‐12,16,17‐hexahydro‐13‐azacyclopenta[a]phenanthrene. These two compounds were then converted to XIX and XXII. The former compound is a salt of (+) 3‐desoxy‐17‐desoxo‐13‐azaequilenin.
The syntheses of 5,6‐dihydroxyindole and some of its derivatives
Authors: Benigni Joseph D. , Minnis R. L.
Published: March 2009

5,6‐Dihydroxyindole (VIa) and its two mono O‐methyl analogs (VIb,c), and their 2‐carboxylic acids (XII), tryptamines (XV), and N‐acetyltryptamines (XVII) have been synthesized. An improved syntheses of the 5,6‐dihydroxyindoles has been developed.
Ten π‐electron nitrogen heterocyclic compounds III: The synthesis and NMR spectra of some 1,6‐naphthyridines
Authors: Paudler William W. , Kress Thomas J.
Published: March 2009

The synthesis of 1,6‐naphthyridine and of some 4‐substituted 1,6‐naphthyridines are described. The analysis of the NMR spectra and a correlation between the chemical shifts of H2, H5, H7, H8, and Brown's σp+ values are reported.
Heterocyclic intermediates for the preparation of thermally stable polymers
Authors: Preston J.
Published: March 2009

A number of heterocyclic intermediates useful for the preparation of thermally stable polymers are reported with their physical properties. Most of the intermediates described are new compounds, while others have been reported previously but without physical properties. Improvements in the syntheses of several of the substances reported earlier are given.
Correlation of NMR chemical shifts of 2‐methyl protons of substituted benzazoles with hammett's substituents constants
Authors: Di Modica Gaetano , Barni Ermanno , Gasco Alberto
Published: March 2009

The chemical shifts of 2‐methyl protons of twenty one 5‐ and 6‐ substituted benzazoles determined in carbon tetrachloride solution, were plotted against the Hammett substituent constants using δm for groups in the 5‐ position and δp for groups in the 6‐ position, obtaining satisfactory linear correlations. These results are taken to indicate that electronic effects are transmitted to the 2‐position predominantly through the nitrogen atom and that virtually no transmission occurs through the hetero atom. The deshielding effect of the hetero atom is opposite to the electronegativity and this may be qualitatively explained in terms of different aromaticity of these heterocycles.
2,4,8,10‐Tetraoxa‐3,9‐diphosphaspiro[5.5]undecane‐3,9‐disulfide and Some Derived Compounds
Authors: Rätz Rudi , Bliss Arthur D.
Published: March 2009

2,4,8,10‐Tetraoxa‐3,9‐diphosphaspiro[5.5]undecane‐3,9‐disulfide (I) has been prepared by the treatment of 3, 9‐dichloro‐2,4,8,10‐tetraoxa‐3,9‐diphosphaspiro[5.5]undecane (II) with hydrogen sulfide. The reactions of I with thiocyanates to give esters of 3,9‐dimercapto‐2,4,8,10‐tetraoxa‐3,9‐diphosphaspiro[5.5]undecane‐3, 9‐disulfide (III) and with isocyanates and isothiocyanates to give P‐carbamoyl and thiocarbamoyl derivatives of I were investigated. I was also found to condense with chloral to produce an α‐hydroxy‐thiophosphonate (XXVIII), but similar reactions with other aldehydes failed to yield analogous products.
Thiazolo [3,2‐a] pyridinium salts
Authors: Bradsher C. K. , Lohr D. F.
Published: March 2009

The sulfides formed by the reaction of α‐halo ketones or α‐halo acetals with 2‐mercaptopyridine may be cyclized in good yield to form thiazolo[3, 2‐a]pyridinium salts. The presence of chloro or nitro substituents on the pyridine ring does not interfere with the synthesis. Nitration of 3‐methylthiazolo[3, 2‐a]pyridinium perchlorate has been found to occur at position 8.
Ten‐π ‐ electron nitrogen heterocyclic compounds. VIII. Semi‐empirical calculations of chemical‐shifts of ring‐protons and of methyl‐protons
Authors: Paudler William W. , Kuder James E.
Published: March 2009

The chemical‐shifts of the ring protons and of the methyl protons of some unsub‐stituted and some methylpolyazanidenes have been calculated by a semi‐empirical method utilizing charge‐densities obtained from HMO calculations. The success of this method lies in the choice of the reference compound, pyrrocoline.
Benzo[b]thiophene derivatives. VIII. Benzo[b]thiophene‐3‐earboxaldehyde and derivatives
Authors: Campaigne E. , Neiss E. S.
Published: March 2009

A procedure for the preparation of benzo[b]thiophene‐3‐carboxaldehyde from 3‐methyl‐benzo[b]thiophene is reported. This aldehyde behaves as a typical reactive aromatic aldehyde with respect to oxidation, reduction, the mixed Cannizzaro reaction, reductive amination and acyloin and other condensation reactions.
Tautomeric structure of 1‐Oxy‐2‐phenylbenzimidazole
Authors: Stacy Gardner W. , Wollner Thomas E. , Oakes Thomas R.
Published: March 2009

The synthesis of 3‐methyl‐2‐phenylbenzimidazole‐1‐oxide (VIII) has been accomplished. Consequently, it has been possible to establish the tautomeric structure of I as 1‐hydroxy‐2‐phenylbenzimidazole (Ia). Contrary to recent observations on the parent 1‐oxybenzimidazole (IV), I shows no tendency to exist as an N‐oxide (Ib) in aqueous solution.
Physical and chemical properties of hydroxyflavones. V. Deuteroxyflavones from acetoxyflavones by imidazole‐catalyzed deacetylation
Authors: Looker J. H. , Kagal S. A. , Edman J. R.
Published: March 2009

A recently described procedure for imidazole‐catalyzed deacetylation of acetoxyflavones has been modified by effecting hydrolysis in a mixture of deuterium oxide and deuterioethanol (C2H5OD), or in deuterium oxide and deuteriomethanol (CH3OD). Application of the new procedure to monoacetoxyflavones has resulted in the monodeuteroxyflavone. 5‐Deuteroxyflavone has been obtained also by hydrolysis of a rubidium salt in deuterium oxide. Imidazole‐catalyzed hydrolysis of four diacetoxyflavones in a mixture of deuteriomethanol and deuterium oxide is described. Infrared spectral data are presented for the deuteration products, with emphasis on OD stretching and vibrational modes. Comparison of spectra of appropriate monohydroxyflavones and monodeuteroxyflavones permits assignment of δ (OH) bands in four hydroxyflavone spectra.
The reaction of phosphorus pentasulfide with halogen‐substituted nitrogen heterocycles
Authors: Castle Raymond N. , Kaji Kenji , Gerhardf G. Anne , Guither William D. , Weber Celia , Malm Miriam P. , Shoup Regitze R. , Rhoads William D.
Published: March 2009

The novel nucleophilic displacement of halogen by sulfur, by the use of phosphorus pentasulfide in boiling pyridine has been shown to be a general reaction for activated halogen nitrogen heterocycles.
Reaction of inorganic cyanates with halides. II. Reactions of chlorohydrins
Authors: Phillips Brian L. , Argabright Perry A.
Published: March 2009

The reaction of ethylene and trimethylene chlorohydrins with cyanate ion in anhydrous dimethylformamide (DMF) forms 2‐oxazolidinone and tetrahydro‐2H‐1, 3‐oxazin‐2‐one, respectively. These are the major products over a wide concentration range, and at initial chlorohydrin concentration of 1 M and lower, the yields are high enough to make the reaction useful for synthesis of oxazine and oxazolidine derivatives. The corresponding reaction with tetramethylene chlorohydrin gave tetrahydrofuran as the major product with the by‐products being polymeric. Pentamethylene and hexamethylene chlorohydrins yield linear polyurethanes when allowed to react with cyanate in DMF. Examination of the relative rates of reaction of these chlorohydrins indicate that the mechanism by which urethanes are formed (both cyclic and polymeric) is an SN2 displacement of chloride by cyanate ion to give an isocyanate intermediate which then reacts with an alcohol group to form urethane.
A convenient preparation of indoline
Authors: Dolby Lloyd J. , Gribble Gordon W.
Published: March 2009

An efficient method for chemically reducing indole to indoline using zinc dust and 85% phosphoric acid is described. 2, 3‐Dimethylindole, 1,2,3, 4‐tetrahydrocarbazole and N‐methyl‐l,2,3,4‐tetrahydrocarbazole are also reduced to the corresponding dihydroindoles in somewhat lower yields. Unlike earlier acid‐metal reductions of indole little or no polymerization is observed.