bluuebunny/crossref_metadata_2025_split huggingface dataset:
Reactions 1‐acetyl‐3‐oxo‐2,3‐dihydroindole with alkyl 2‐cyano‐3‐alkoxypropenoate and alkyl 2‐alkoxycarbonyl‐3‐alkoxy‐propenoate. Synthesis of 9‐acetoxypyrrolo[1,2‐a]indol‐3‐one derivatives
Authors: Mérour J. Y. , Piroëlle S. 
Published: May 2009

Abstract1‐Acetyl‐3‐oxo‐2,3‐dihydroindole reacted with methyl 2‐cyano‐3‐methoxypropenoate and ethyl 2‐cyano‐3‐ethoxypropenoate in the presence of sodium hydride, affording compounds 3 (2‐(2‐cyano‐2‐alkoxycarbonyl‐vinyl)‐3‐hydroxyindole). Methyl 2‐methoxycarbonyl‐3‐methoxypropenoate gave compounds 4 or compounds 5 (in the presence of Triton B). Heating compounds 3 or their acetylated derivatives in acetic anhydride at reflux afforded 9‐acetoxy‐(3H)‐pyrrolo[1,2‐a]indol‐3‐one 8.
Reactions of 3‐oxo‐2,3‐dihydrobenzofuran with alkyl 2‐cyano‐3‐alkoxypropenoate and alkyl 2‐alkoxycarbonyl‐3‐alkoxypropenoate. Synthesis of pyran derivatives
Authors: Mérour J. Y. , Cossais F. 
Published: May 2009

Abstract3‐Oxo‐2,3‐dihydrobenzofuran reacted with ethyl 2‐cyano‐3‐ethoxypropenoate, methyl 2‐cyano‐3‐methoxy‐propenoate affording compounds 3 (2‐(2‐cyano‐2‐alkoxycarbonylvinyl)‐3‐hydroxybenzofuran) obtained as a mixture of Z + E isomers. Methyl 2‐methoxycarbonyl‐3‐methoxypropenoate gave compound 4. Malonic compounds added on 2‐dimethylaminomethylene‐3‐oxo‐2,3‐dihydrobenzofuran 6 for giving compound 3 or 2‐oxo‐3‐methoxycarbonyl‐2H‐pyrano[3,2‐b]benzofuran 8. Compound 8 was also obtained by heating compound 4 in xylene.
Réarrangement de thiénobenzothiépinones en thiénoisothiazolinone et benzoisothiazolinone
Authors: Daich Abdelali , Decroix Bernard 
Published: May 2009

AbstractDans les conditions de la réaction de Schmidt les thiénobenzothiépinones 1, 2 et 13 subissent un réarrangement respectivement en N‐benzylthiéno[2,3‐d]isothiazolin‐3‐one (5) et benzoisothiazolin‐3‐one (6). Un mécanisme de ce réarrangement est proposé.
Pyrimidine derivatives. VI. Synthesis of mono‐, di‐, tri‐, and tetrabromo‐substituted pyrimidine derivatives
Authors: Kinoshita Toshio , Okunaka Tomoko , Ohwada Takehiro , Kawanaka Hiroyuki , Furukawa Sunao 
Published: May 2009

AbstractThe following bromo‐2,4(1H,3H)‐pyrimidinediones possessing a bromo substituent at the 5‐position and side chains at the 1‐ and 6‐positions were prepared. The three types of mono‐bromo derivatives are: 1‐(bromoalkyl)‐3,6‐dimethyl‐ 3a‐d, 5‐bromo‐3,6‐dimethyl‐1‐(hydroxyalkyl)‐ 4a‐d, and 1‐(acetoxyalkyl)‐5‐bromo‐3,6‐dimethyl‐2,4(1H,3H)‐pyrimidinediones 11a‐d. The three types of dibromo derivatives are: 5‐bromo‐1‐(bromoalkyl)‐3,6‐dimethyl‐ Sa‐d, 1‐(acetoxyalkyl)‐5‐bromo‐6‐bromomethyl‐ 8a, 8c, and 8d, and 5‐bromo‐6‐bromomethyl 1‐(hydroxyalkyl)‐2,4(1H,3H)‐pyrimidinediones 9a, 9c, and 9d. Likewise one group of tribromo and one group of tetrabromo derivatives are: 5‐bromo‐1‐(bromoalkyl)‐6‐bromomethyl‐7a‐d and 5‐bromo‐1‐(bromoalkyl)‐6‐dibromomethyl‐2,4(1H,3H)‐pyrimidinediones 6a‐d.
A convenient route to diazepines by intramolecular cyclisation of carbonylazides
Authors: Daich Abdelali , Povazanec Frantisek , Decroix Bernard 
Published: May 2009

AbstractThe appropriate substituted carbonylazides I treated with warm acetic acid give the corresponding acetamide IV or the cyclic lactam VI. This is a convenient route to 10,11‐Dihydro‐5H‐pyrrolo[1,2‐a][1,4]‐benzodiazepin‐11‐one and 10,11‐Dihydro‐4H‐thieno[2,3‐e]pyrrolo[1,2‐a][1,4]diazepin‐10‐one.
Synthesis and properties of 5‐(1,2‐dihaloethyl)‐2′‐deoxyuridines and related analogues
Authors: Kumar Rakesh , Knaus Edward E. , Wiebe Leonard I. 
Published: May 2009

AbstractThe regiospecific reaction of 5‐vinyl‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (2) with HOX (X = Cl, Br, I) yielded the corresponding 5‐(1‐hydroxy‐2‐haloethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridines 3a‐c. Alternatively, reaction of 2 with iodine monochloride in aqueous acetonitrile also afforded 5‐(1‐hydroxy‐2‐iodoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (3c). Treatment of 5‐(1‐hydroxy‐2‐chloroethyl)‐ (3a) and 5‐(1‐hydroxy‐2‐bromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (3b) with DAST (Et2NSF3) in methylene chloride at ‐40° gave the respective 5‐(1‐fluoro‐2‐chloroethyl)‐ (6a, 74%) and 5‐(1‐fluoro‐2‐bromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (6b, 65%). In contrast, 5‐(1‐fluoro‐2‐iodoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (6e) could not be isolated due to its facile reaction with methanol, ethanol or water to yield the corresponding 5‐(1‐methoxy‐2‐iodoethyl)‐ (6c), 5‐(1‐ethoxy‐2‐iodoethyl)‐ (6d) and 5‐(1‐hydroxy‐2‐iodoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (3c). Treatment of 5‐(1‐hydroxy‐2‐chloroethyl)‐ (3a) and 5‐(1‐hydroxy‐2‐bromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (3b) with thionyl chloride yielded the respective 5‐(1,2‐dichloroethyl)‐ (6f, 85%) and 5‐(1‐chloro‐2‐bromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (6g, 50%), whereas a similar reaction employing the 5‐(1‐hydroxy‐2‐iodoethyl)‐ compound 3c afforded 5‐(1‐methoxy‐2‐iodoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (6c), possibly via the unstable 5‐(1‐chloro‐2‐iodoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine intermediate 6h. The 5‐(1‐bromo‐2‐chloroethyl)‐ (6i) and 5‐(1,2‐dibromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (6j) could not be isolated due to their facile conversion to the corresponding 5‐(1‐ethoxy‐2‐chloroethyl)‐ (6k) and 5‐(1‐ethoxy‐2‐bromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (61). Reaction of 5‐(1‐hydroxy‐2‐bromoethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (3b) with methanolic ammonia, to remove the 3′,5′‐di‐O‐acetyl groups, gave 2,3‐dihydro‐3‐hydroxy‐5‐(2′‐deoxy‐β‐D‐ribofuranosyl)‐furano[2,3‐d]pyrimidine‐6(5H)‐one (8). In contrast, a similar reaction of 5‐(1‐fluoro‐2‐chloroethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridine (6a) yielded (E)‐5‐(2‐chlorovinyl)‐2′‐deoxyuridine (1b, 23%) and 5‐(2′‐deoxy‐β‐D‐ribofuranosyl)furano[2,3‐d]pyrimidin‐6(5H)‐one (9, 13%). The mechanisms of the substitution and elimination reactions observed for these 5‐(1,2‐dihaloethyl)‐3′,5′‐di‐O‐acetyl‐2′‐deoxyuridines are described.
A phenolic glycoside from artemisia sacrorum
Authors: Konda Yaeko , Funato Nobuyuki , Harigaya Yoshihiro , Li Xian , Zhang Dezhi , Onda Masayuki 
Published: May 2009

AbstractA phenolic glycoside has been isolated from Artemisia sacrorum grown in the Northeast of China. This compound is identified to be 4‐O‐β‐D‐glucopyranosyl‐2‐O‐methylphloroacetophenone by means of nmr spectroscopy and synthesis.
Novel heterocyclization of 4‐phenylthiosemicarbazones and related compounds with chlorocarbonylsulfenyl chloride
Authors: Kabashima Shigeru , Okawara Tadashi , Yamasaki Tetsuo , Furukawa Mitsuru 
Published: May 2009

AbstractChlorocarbonylsulfenyl chloride was allowed to react with 1‐alkylidene‐4‐phenylthiosemicarbazones in the presence of triethylamine to give 1,2,4‐triazolines, whereas with 1‐arylidene‐4‐phenylthiosemicarbazones to afford 1,2,4‐dithiazolidines. Treatment of diarylidenethiocarbohydrazides and diarylidenaminoguanidines with chlorocarbonylsulfenyl chloride under similar conditions gave 1,2,4‐dithiazolidines and 1,2,4‐thiadiazolidines, respectively.
Synthesis of 4‐hydroxy‐3‐triftuoromethylpyrazoles
Authors: Iwata Satoru , Namekata Junji , Tanaka Kiyoshi , Mitsuhashi Keiryo 
Published: May 2009

AbstractTrifluoroacetaldehyde hydrazones are condensed with glyoxals to give 4‐hydroxy‐3‐trifluoromethylpyrazoles, the reaction offering a novel route to 4‐hydroxypyrazoles carrying trifluoromethyl group. The 4‐hydroxyl group was easily converted to its derivatives by the reaction with various electrophiles.
Inhibition of human dihydrofolate reductase by 2,4‐diaminoquinazolines bearing simple substituents on the aromatic ring
Authors: Hynes John B. , Tomažič Alenka , Kumar Arvind , Kumar Veena , Freisheim James H. 
Published: May 2009

AbstractA series of thirty eight 2,4‐diaminoquinazolines having diverse substitution patterns on the aromatic ring was evaluated for inhibitory activity against dihydrofolate reductase (DHFR) obtained from a human lymphoblast cell line. Many of these compounds were also evaluated as inhibitors of rat liver DHFR under the same experimental conditions. In most instances the results obtained with each enzyme were comparable indicating that the rodent enzyme is a suitable model for the human DHFR as far as the determination of I50 values is concerned. The results demonstrate that relatively simple 5‐substituted‐ or 5,6‐disubstituted‐2,4‐diaminoquinazolines can be potent DHFR inhibitors. The presence of a nonpolar substituent at position 7 or 8 was highly detrimental to inhibitory potency.
The fragmentation behavior of differently substituted 2‐amino‐1,3,4‐benzotriazepines
Authors: Vainiotalo P. , Ottoila P. , Morgenstern O. , Richter P. 
Published: May 2009

AbstractThe mass spectra of eighteen 2‐amino‐1,3,4‐benzotriazepines were recorded under electron ionization, and the fragmentation patterns were elucidated by metastable ion analysis and exact mass measurements. The most typical fragmentations were ring contraction reactions with the loss of nitrogen atoms at positions 3 and 4. Extensive rearrangement reactions took place as well. In these the substituted 2‐amino group played an important role. Isomeric compounds were easily distinguished.
Ground state vs. transition state substituent effects on reactions of aziridinium salts
Authors: Crist Delanson R. , Turujman Saleh A. , Hashmall Joseph A. 
Published: May 2009

AbstractThe possibility that the similarity of Hammett ρ values for several very different reactions of 2‐arylaziridinium salts is due to ground state effects was investigated by MO methods and ESCA. Minimum energy structures of p‐nitrophenyl‐, phenyl‐, and p‐methoxyphenyl‐substituted ions, however, have the same C2N bond lengths. This result shows that substituent effects are primarily a transition state phenomenon, even in the three‐membered ring heterocycles. In agreement, the ground state does not have significant amino carbocation character based on similar charge distributions of 2‐phenyl‐N,N‐dimethylaziridinium ion and N,N,N‐trimethylbenzylammonium ion as well as the same nitrogen ls binding energies by ESCA studies on corresponding salts.
The synthesis of novel polycyclic heterocyclic ring systems via photocyclization. 6. Naphthothienonaphthyridines
Authors: Castle Raymond N. , Pakray Sudabeh , Martin Gary E. 
Published: May 2009

AbstractFive novel polycyclic heterocyclic ring systems are reported via photocyclization. The specific final products in these ring systems are: naphtho[1′,2′:4,5]thieno[2,3‐c][1,8]naphthyridin‐6(5H)‐one (5), naphtho‐[1′,2′:4,5]thieno[2,3‐c][1,6]naphthyridin‐6(5H)‐one (6), naphtho[1′,2′:4,5]thieno[2,3‐c]‐1,5‐naphthyridine (9), naphtho[1′,2′:4,5]thieno[2,3‐c][1,2,4]triazolo[4,3‐a]‐1,5‐naphthyridine (12), and naphtho[2′,1′:4,5]thieno[2,3‐c]‐1,5‐naphthyridine (17). The direction of photocyclization to produce 9 was established from a zero quantum two‐dimensional nmr spectroscopy experiment (ZQCOSY) using 6‐chloronaphtho[1′,2′:4,5]thieno[2,3‐c]‐1,5‐naphthyridine (8) as the model compound.
A convenient synthesis of (2‐styrylchromon‐8‐yl)acetic acids
Authors: Zammattio F. , Brion J. D. , Belachmi L. , Le Baut G. 
Published: May 2009

Abstract(2‐Styrylchromon‐8‐yl)acetic acids, structural analogs of (flavon‐8‐yl)acetic acid (FAA) have been synthesized with satisfactory yields according to two different methods. The 1H and 13C nmr data fovor the S‐trans stereoisomers.
Synthesis of 2‐guanyl‐4‐(3‐substituted‐phenyl)thiazoles with potent histamine H2‐antagonism activity
Authors: Santilli Arthur A. , Scotese Anthony C. , Morris Robert L. , Bell Stanley C. 
Published: May 2009

AbstractThe syntheses of novel 2‐guanyl‐4‐(3‐substituted‐phenyl)thiazoles showing potent histamine H2‐antagonism activity is reported. The most potent compound is 17 where the substitution at the 3‐position of the phenyl ring is an N‐methylamidino function.
Synthesis of 6,6‐disubstituted penems
Authors: Rossi Tino , Andreotti Daniele , Tamburini Bruno , Marchioro Carla 
Published: May 2009

AbstractThe synthesis of a series of 6,6‐disubstituted penems starting from penicillanate 5a is described. These penems were isolated and characterized as their pivaloyloxy methyl ester.
Synthesis of 2H‐pyrazolo[3,4‐b]pyridin‐3‐oles via cyclization of pyrazolacrylonitriles
Authors: Cocco Maria Teresa , Congiu Cenzo , Onnis Valentina 
Published: May 2009

AbstractThe reaction of 1‐acyl‐3‐amino‐5‐pyrazolones 1 with ethyl ethoxymethylenecyanoacetate and ethoxymethylenemalononitrile 2 is described. Thermal cyclization in phenyl ether of the obtained pyrazol‐acrylonitriles 3 provides good yields of pyrazolopyridin‐3‐ol derivatives 4.
Synthesis of 5′‐azido‐ and 5′‐amino‐2′,5′‐dideoxynucleosides from quinazoline‐2,4(1H,3H)‐diones
Authors: El‐Barbary Ahmed A. , El‐Brollosy Nasser R. , Pedersen Erik B. , Nielsen Claus 
Published: May 2009

AbstractQuinazoline‐2,4(1H,3H)‐diones 4 were silylated and condensed with methyl 5‐azido‐2,5‐dideoxy‐3‐O‐(4‐methylbenzoyl)‐α,β‐D‐erythro‐pentofuranoside (3) using trimethylsilyl trifluoromethanesulfonate (TMS triflate) as the catalyst to afford the corresponding 5′‐azidonucleosides 5. 1‐(5‐Azido‐2,5‐dideoxy‐α‐D‐erythro‐pentofuranosyl)quinazoline‐2,4(1H,3H)‐diones 6 and the corresponding β anomers were obtained by treating 5 with sodium methoxide in methanol at room temperature. 6‐Methyl‐1‐(5‐amino‐2,5‐dideoxy‐β‐D‐erythro‐pentofuranosyl)quinazoline‐2,4(1H,3H)‐dione (8) was obtained by treatment of the corresponding azido derivative 7 with triphenylphosphine in pyridine, followed by hydrolysis with ammonium hydroxide.
Intramolecular photocycloadditions of 6,6′‐dimethyl‐4,4′‐polymethylenedioxy‐di‐2‐pyrones
Authors: Shimo Tetsuro , Ueda Shinichi , Suishu Takaaki , Somekawa Kenichi 
Published: May 2009

AbstractPhotosensitized reactions of 4,4′‐polymethylene‐di‐2‐pyrones 2b‐e afforded [2+2]‐cycloadducts 3‐5, site‐selectively. The selectivity depended upon the methylene chain length. Namely, the three carbon chain gave a syn head‐to‐head adduct 3b at the 3,4‐position of the 2‐pyrone ring, the four to six carbon chains gave syn head‐to‐head adducts 4c‐e at the 5,6‐position and/or anti head‐to‐head adducts 5d,e at the 5,6‐position, respectively. The intramolecular cycloaddition mechanism was also explained from results calculated by means of PM3‐CI method.
Haloacetylated enol ethers. 5 [5]. Heterocyclic ring closure reactions of β‐alkoxyvinyl dichloromethyl ketones with hydroxylamine
Authors: Martins Marcos A. P. , Zoch Alana N. , Flores Alex F. C. , Clar Günter , Zanatta Nilo , Bonacorso Helio G. 
Published: May 2009

AbstractThe β‐alkoxyvinyl dichloromethyl ketones 1a‐d are cyclocondensed with hydroxylamine hydrochloride in pyridine to afford the 5‐hydroxy‐5‐dichloromethyl‐4,5‐dihydroisoxazoles 2a‐d in good yield. The cyclo‐condensation of compound 1c gave, together with 2c, 3‐cyano‐2‐hydroxy‐2‐dichloromethyltetrahydrofuran 5c. The dehydratation of compounds 2a,b, derived from acyclic enol ethers, with concentrated sulfuric acid at 30°, led the corresponding 5‐dichloromethylisoxazoles 3a,b. The dehydratation of compounds 2c,d, derived from cyclic enol ethers, with concentrated sulfuric acid at 30°, led the bicyclic 4,5‐dihydroisoxazoles 4c,d, and at 55°, a competitive rearrangement reaction gives the 3‐cyano‐2‐hydroxy‐2‐dichloromethyl‐2H‐pyran 5d.
Synthesis of the cardiotonic bemarinone, 5,6‐dimethoxy‐4‐methyl‐2(1H)‐quinazolinone, utilizing a directed metalation approach
Authors: Conley Richard A. , Barton Donald L. , Stefanick Stephen M. , Lam Margaret M. , Lindabery Gregory C. , Kasulanis Charles F. , Cesco‐Cancian Sergio , Currey Stephen , Fabian Arthur C. , Levine Seymour D. 
Published: May 2009

AbstractSeveral methods for the synthesis of bemarinone, 5,6‐dimethoxy‐4‐methyl‐2(1H)‐quinazolinone, were explored with the most successful being a directed metalation route. Details of the lithiation and the subsequent reaction with electrophiles of 3′,4′‐dimethoxy‐2,2‐dimethylpropioanilide and other derivatives of 3,4‐dimethoxyaniline are given.
Pyridine‐substituted hydroxythiophenes. V. Preparation of 5‐(2‐, 3‐and 4‐pyridyl)‐2‐hydroxythiophenes
Authors: Zhang Yihua , Hömfeldt Anna‐Britta , Gronowitz Salo 
Published: May 2009

Abstract5‐(2‐, 3‐ and 4‐Pyridyl)‐2‐t‐butoxythiophenes have been prepared in very good yields by Pd(0) catalyzed cross‐coupling of the three isomeric bromopyridines with 5‐trimethylstannyl‐2‐t‐butoxythiophene derived from 2‐bromothiophene via 2‐t‐butoxythiophene. Dealkylation of 5‐(2‐, 3‐ and 4‐pyridyl)‐2‐t‐but‐oxythiophenes with boron trifluoride etherate in dichloromethane at room temperature led to predominant formation of rearranged products, 5‐(2‐ and 3‐pyridyl)‐3‐t‐butyl‐3‐thiolene‐2‐ones, together with a small amount of 5‐(2‐ and 3‐pyridyl)‐2‐hydroxythiophenes as a mixture of two tautomeric keto forms in the case of the 2‐pyridyl and the 3‐pyridyl isomers, and exclusive formation of rearranged product in the case of the 4‐pyridyl isomer.However, dealkylation of 2‐methoxy‐5‐(2‐, 3‐ and 4‐pyridyl)thiophenes, prepared similarly to the 5‐(2‐, 3‐ and 4‐pyridyl)‐2‐t‐butoxythiophenes, with boron tribromide under the same reaction conditions as above resulted exclusively in the tautomeric mixture of 5‐(2‐ and 3‐pyridyl)‐3‐thiolene‐2‐ones and 5‐(2‐ and 3‐pyridyl)‐4‐thiolene‐2‐ones in the case of the 2‐pyridyl and 3‐pyridyl isomers. In the case of the 4‐pyridyl isomer polymerization took place.
The preparation of intercalating isoxazoles via a nitrile oxide cycloaddition
Authors: Mosher Michael D. , Natale Nicholas R. 
Published: May 2009

AbstractPyridinium chlorochromate oxidation of 9‐methylacridine (2) affords the corresponding aldehyde 3 in good yield. Conversion of the aldehyde to the hydroximinoyl chloride 5a was accomplished via reaction of the corresponding oxime with N‐chlorosuccinimide. Dipolar addition to the enamine of ethylacetoacetate provided the corresponding isoxazoles 1 in good yield.
Synthesis of 1,2,3‐triazolo[1,5‐a]pyridine ester derivatives
Authors: Latham Elliot J. , Stanforth Stephen P. 
Published: May 2009

AbstractLithiation of 1,2,3‐triazolo[1,5‐a]pyridines 4b and 4c with lithium diisopropylamide (LDA) gave the corresponding lithio derivatives 5b and 5c from which esters 6b and 6c were obtained by treatment with carbon dioxide and then dimethyl sulfate. Lithio derivatives 5a‐5c reacted with DMF giving aldehydes 7a‐7c. Esters 9a‐9c were prepared from aldehydes 7a‐7c and carbomethoxymethylenetriphenylphosphorane.
Synthesis of pyrido[3,4‐d] benzazepines
Authors: Kunick Conrad , Link Andreas 
Published: May 2009

AbstractThe synthesis of some derivatives of the novel heterocyclic ring system pyrido[3,4‐d][1]benzazepine is reported. Thus, pyrido[3,4‐d][1]benzazepin‐7‐one 6 was prepared by cyclisation of the Michael adduct 5 with ammonium ferric sulfate. Reaction of 6 with phosphorus pentasulfide gave the thiolactam 7, which after methylation and subsequent reaction with amines furnished the amidines 10.
Synthesis of some oxadiazole derivatives of d‐mannose
Authors: Fascio Mirta L. , D'Accorso Norma B. 
Published: May 2009

AbstractThe syntheses of 2‐methyl‐5‐[1′,2′,3′,4′,5′‐penta‐O‐benzoyl‐D‐manno‐pentitol‐1′‐yl]‐1,3,4‐oxadiazole and 5‐methyl‐3‐[1′,2′,3′,4′,5′‐penta‐O‐benzoyl‐D‐manno‐pentitol‐1‐′yl]‐1,2,4‐oxadiazole, as well as their intermediate products, are described. Their 1H and 13C nmr and ms spectra are presented and their preferential conformation in solution are proposed.
Synthesis of 8,9‐dihydrodipyrazolo[3,4‐b:4′,3′‐f][1,5]diazocin‐10(1H)‐one. A new ring system
Authors: Migliara Onofrio , Lamartina Liliana , Timoneri Marina , Plescia Salvatore 
Published: May 2009

Abstract8,9‐Dihydrodipyrazolo[3,4‐b:4′,3′‐f][1,5]diazocin‐10(1H)‐ones 7 were prepared by cyclization of 1‐ethyl‐N,3‐dimethyl‐4‐acetamido‐N‐(1‐R1‐3‐R2‐1H‐pyrazol‐5‐yl)‐1H‐pyrazole‐5‐carboxamides 6 by a Bischler‐Napieralski cyclization. A complete assignment of the chemical shifts to the carbon atoms of compound 7 was performed by different nmr experiments, such as DEPT and XHDEPT for onebond CH correlations and COLOC experiments for long‐range C‐H correlations.
Synthesis of 3H‐thieno[3,2‐c]‐1,2‐dithiole‐3‐thione and its reaction with n‐butylamine
Authors: Pregnolato Massimo , Borgna Pietro , Terreni Marco 
Published: May 2009

AbstractA convenient synthesis of 3H‐thieno[3,2‐c]‐1,2‐dithiole‐3‐thione (7) is proposed. The reaction of 7 with n‐butylamine afforded the N‐butylthieno[3,2‐c]isothiazole‐3(2H)‐thione (7a) in dynamically equilibrium [1] with its 3H‐thieno[3,2‐c]‐1,2‐dithiole‐N‐butyl‐3‐imino isomer 7b. Characterizations and antimicrobial activities of the synthesized products are reported.
Synthesis of trans‐7‐hydroxymethyl‐2‐(2‐benz[d]isoxazol‐3‐yl)octahydro‐2H‐pyrido[1,2‐a]pyrazine
Authors: Urban Frank J. 
Published: May 2009

AbstractAn efficient synthesis of trans‐7‐hydroxymethyl‐2‐(2‐benz[d]isoxazol‐3‐yl)octahydro‐2H‐pyrido[1,2‐a]‐pyrazine 2 is presented which relies on the equilibration of cis‐dimethyl piperidinedicarboxylate followed by alkylation with phthalimidoethyl triflate.
On the syntheses of 8‐Heteroaryl‐substituted 9‐(β‐D‐Ribofuranosyl)‐2,6‐diaminopurines through Pd‐catalyzed coupling in the presence of cupric oxide
Authors: Ozola Vita , Persson Tina , Gronowitz Salo , Hörnfeldt Anna‐Britta 
Published: May 2009

AbstractConvenient methods for the preparation of 9‐(β‐D‐ribofuranosyl) derivatives of 8‐(2‐ and 3‐thienyl)‐2,6‐diaminopurine and of 8‐(2‐ and 3‐furyl)‐2,6‐diaminopurine, which are potential antiviral agents has been worked out. The key step was a Pd(0)‐catalyzed Stille coupling between 2‐ and 3‐tributylstannylthiophene and 2‐ and 3‐tributylstannylfuran and trimethylsilyl protected 9‐(β‐D‐ribofuranosyl)‐2,6‐diamino‐8‐bro‐mopurine. The use of N,N‐dimethylformamide as solvent at 110° and dichloro(diphenylphosphine‐propane)palladium(II) [PdC12(dppp)] with cupric oxide as co‐reagent was essential in order to obtain a fast reaction and high yields.
A short synthesis of C‐glycosyl pyrazoles and pyrroles
Authors: Del Valle José L. , Polo Cecilia , Torroba TomÁS , Marcaccini Stefano 
Published: May 2009

AbstractThe sodium salt of TOSMIC reacted with (E)‐3,4,5,6,7‐penta‐O‐acetyl‐1,2‐dideoxy‐1‐C‐nitro‐D‐galacto‐ (1) and ‐D‐manno‐hept‐1‐enitol (2) to give 3‐(D‐galacto‐ (3) and 3‐(D‐manno‐penta‐O‐acetylpentitol‐1‐yl)‐4‐nitropyrrole (4), respectively. Compound 1 reacted with diaryl nitrile imines, affording 1,3‐diaryl‐4‐(1,2,3,4,5‐penta‐O‐acetyl‐D‐galacto‐pentitol‐1‐yl)pyrazoles 5 and 6.
Synthesis of aryl 2‐(2‐imidazolyl)ethyl ketones
Authors: Abdelaal Salma M. , Kim Jang‐Woo , Bauer Ludwig 
Published: May 2009

AbstractThe Claisen‐Schmidt condensation of 1‐(triphenylmethyl)‐2‐imidazolecarboxaldehyde with acetophenones yielded 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]propen‐1‐ones 7. Selective catalytic hydrogenation over platinum of 7 furnished 1‐aryl‐3‐(2‐imidazolyl)‐1‐propanones 8. An alternate synthesis of 8 started with sodium borohydride reduction of 7 to give allylic alcohols, 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]‐2‐propen‐1‐ols 10, which were rearranged by hot aqueous sodium to 8. Acid hydrolysis of 8 provided the title compounds and triphenylmethanol.
Oxidation of 5‐hydroxymethylfurfural and derivatives to furanaldehydes with 2,2,6,6‐tetramethylpiperidine oxide radical ‐ co‐oxidant pairs
Authors: Cottier Louis , Descotes Gérard , Viollet Estelle , Lewkowski Jaroslaw , Skowroñski Romuald 
Published: May 2009

AbstractThe oxidation of 5‐hydroxymethylfurfural (1) or 5‐hydroxymethylfurfurylideneacetophenone (4) with various 4‐substituted 2,2,6,6‐tetramethylpiperidine radicals (TEMPO) 3a‐d and supporting co‐oxidants gave corresponding aldehydes 2 or 5 in fair yields.
Synthesis of cyclic and acyclic nucleoside analogues having a thiophene or dihydrothiophene ring fused to the d side of an uracil
Authors: Jourdan Fabrice , Renault Jacques , Karamat Abdesselam , Laduríe Daniel , Robba Max 
Published: May 2009

AbstractSynthesis of cyclic and acyclic nucleosides was achieved by alkylation of various new aglycones following the Vorbrüggen and Niedballa's procedure [6]. The analytical results allowed us to conclude that the alkylation occured on N1 site and led to the β anomeric form for the cyclic nucleosides.