bluuebunny/crossref_metadata_2025_split huggingface dataset:
N,N‐dimethylamino‐functionalized basic ionic liquid catalyzed one‐pot multicomponent reaction for the synthesis of 4H‐benzo[b]pyran derivatives under solvent‐free condition
Authors: Chen Lu , Li Yi‐Qun , Huang Xu‐Jiang , Zheng Wen‐Jie 
Published: March 2009

AbstractA simple, clean, and environmentally benign three‐component process for the synthesis of 4H‐benzo[b]pyran derivatives using basic ionic liquid N,N‐dimethylaminoethylbenzyldimethylammonium chloride ([PhCH2Me2N+CH2CH2NMe2]Cl−) as an efficient catalyst under solvent‐free condition is described. A wide range of aromatic aldehydes easily undergoes condensation with malononitrile and 5,5‐dimethylcyclohexane‐1,3‐dione (dimedone) under solvent‐free condition to afford the desired products of good purity in excellent yields. Taking into account environmental and economical considerations, the protocol presented here has the merits of environmentally benign, simple operation, convenient workup, and good yields. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:91–94, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20516
One‐pot synthesis of primary 1‐aminophosphonates: Coupling reaction of carbonyl compounds, hexamethyldisilazane, and diethyl phosphite catalyzed by Al(OTf)3
Authors: Sobhani Sara , Tashrifi Zahra 
Published: March 2009

AbstractAl(OTf)3 has been utilized as a new and efficient catalyst for the selective synthesis of primary 1‐aminophosphonates by a one‐pot coupling reaction of various types of aldehydes/ketones, hexamethyldisilazane, and diethyl phosphite under solvent‐free conditions. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:109–115, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20517
Sparing the ortho‐position in nucleophilic aromatic substitution‐specific displacement of the 4‐SePh group in 2,4‐bis(phenylseleno)nitrobenzene
Authors: Stuhr‐Hansen Nicolai , Götze Thorstein Finn , Henriksen Lars , Sølling Theis Ivan , Langkilde Annette , Sørensen Henning Osholm 
Published: March 2009

AbstractUpon treatment of o‐ and p‐(phenylseleno)nitrobenzenes with sodium methoxide quantitative exchange reactions took place, affording the corresponding methoxynitrobenzenes. Upon reaction between 2,4‐bis(phenylseleno)nitrobenzene 2 and sodium methoxide, an unusual regiopure formation of 4‐methoxy‐2‐(phenylseleno)nitrobenzene 3 was observed. This product remained unreactive toward an excess of sodium methoxide, thus preventing the formation of 2,4‐dimethoxynitrobenzene 6. The nature of the reactants and of the intermediate Meisenheimer complexes was examined by synthetic investigations, x‐ray crystallography, and DFT calculations. We found that the observed selectivity can be understood in terms of traditional resonance considerations. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:101–108, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20519
A facile preparation of 2‐(2‐arylethyl)‐ and 2‐(aminomethyl)indoles
Authors: Nagarathnam Dhanapalan 
Published: March 2009

AbstractAn important process for the acid catalyzed cleavage of the benzoyl group from 3‐benzoylindoles in high yield is identified and its application for the facile syntheses of 2‐substituted indoles is demonstrated by preparing some 2‐(2‐arylethyl)‐ and 2‐(aminomethyl)indoles from 1,3‐dibenzoyl‐2‐bromomethylindole (7).
Functionalised enaminones and their use in heterocyclic synthesis
Authors: Greenhill John V. , Chaaban Ibrahim , Steel Peter J. 
Published: March 2009

AbstractA series of enaminones derived from 2,4‐dioxocyclohexane carboxylic acid esters has been prepared. The use of some of the new derivatives in the synthesis of some quinazolones and imidazoloquinazolines is illustrated.
Synthesis of substituted 14‐crown‐4 compounds
Authors: Czech Bronislaw P. , Zazulak Wolodymyr , Kumar Anand , Olsher Uriel , Feinberg Hadar , Cohen Shmuel , Shoham Gil , Dalley N. Kent , Bartsch Richard A. 
Published: March 2009

AbstractSeventeen new substituted 14‐crown‐4 derivatives 3‐10, 35‐40, 42, 45 and 46 are described. A series of nine compounds 2‐10 with two, three or four substituents in the 6‐ and/or 13‐positions was synthesized in good yields from the appropriate diols and ditosylates using improved cyclization conditions. The solid state structures of 6,6,13,13‐tetra(benzyloxymethyl)‐14‐crown‐4 (8) and lithium thiocyanate complexes of trans‐ and cis‐6,13‐bis(spiro‐2,2‐dichlorocyclopropyl)‐14‐crown‐4 (45) and (46), respectively, have been determined.
Synthesis of N‐phenylpyrrole and pyrazole amidines and related diamines
Authors: Jarvest Richard L. , Marshall Joanne E. 
Published: March 2009

AbstractN‐Phenylpyrrole and pyrazole nitriles 3,4,10 were prepared in one step from the corresponding aldehydes. The nitriles were converted into novel amidines 5,6,14 and related diamines 7,8,12 were also prepared from the aldehydes. The orientation of the phenyl ring to the basic function was controlled by modifying the torsional angle between the rings by methyl group substitution on the heterocycle.
A short synthesis of 5′‐O‐trityl‐protected threo‐ and erythro‐ 3′‐cyano‐3′‐deoxythymidine epimers using free‐radical chemistry
Authors: Bankston Donald D. , Almond Merrick R. 
Published: March 2009

AbstractA reinvestigation of a synthetic route to 5′‐O‐trityl‐protected erythro‐CNT that incorporates a modification of the Stork radical cyclization‐cyanation reaction generates an unexpected threo‐epimer.
Synthesis of novel bicyclic pyridazine nucleosides
Authors: Lee Sang‐Gyeong , Choi Sam‐Yong , Yoon Yong‐Jin 
Published: March 2009

AbstractThe synthesis of some [6:6]‐ or [6:5]‐fused bicyclic pyridazin‐6‐one nucleosides, starting from 4,5‐dichloro‐3‐nitro(or amino) and 3‐hydrazinopyridazin‐6‐one nucleosides is described.
5,7,12,14‐Tetramethyldimethoxybenzo[b,i][1,4,8,11]tetraazacyclodecine, a new tumoricidal pseudo‐porphyrin
Authors: Czuchajowski Leszek , Morra Matthew , Kubaszewski Eugeniusz , Malinski Tadeusz 
Published: March 2009

AbstractThe title compound, a mixture of two isomers differing in the position of a methoxy substituent in one benzene ring, was obtained in a Ni‐templated synthesis directly as a water soluble dihydrochloride of the free base. The cyclic voltametry study indicated that in a neutral solution the reduction and oxidation are irreversible one electron processes, the latter leading to cation radical undergoing polymerization, a process followed by deposition of a film on the electrode. In 1,2‐dichloroethane the cation radical is oxidized to a dication, both species being much less stable than those originating from meso‐tetraphenylporphyrin. The title compoud at 2.5 × 10−5 M in Tris buffer showed a 50% inhibition of the growth of malignant melanoma cells as compared to a 44% inhibition shown by a water soluble meso‐monomethoxy‐tris(N‐methylpyridinium)porphyrin. The exposure to light for 30 minutes at 2.5 times smaller concentration increased the inhibition caused by the pseudo‐porphyrin from 9% to 49%.
On the oximation of diaryl‐β‐diketones
Authors: Bandiera T. , Grünanger P. , Albini F. Marinone 
Published: March 2009

AbstractThe reaction of asymmetrically substituted β‐diketones with hydroxylamine to give 3,5‐diarylisoxazoles has been re‐investigated, and has been found to occur with a low degree of site‐selectivity unless steric effects are operating. The isoxazole that has the more electron‐deficient aryl group in position 3 is formed preferentially when the reactions are run with hydroxylamine hydrochloride. When the reactions are performed in a neutral medium, a reversed site‐selectivity is observed. Steric effects have a much stronger influence on the selectivity of the reaction: when a substituent is present in the ortho position(s) of the phenyl ring, the heterocycle bearing the ortho‐substituted phenyl group in position 5 is obtained as the sole product both in acidic and in neutral medium.
A new synthetic route to polyaza‐crown macrocycles through the per(N‐formyl)polyaza‐crowns
Authors: Bradshaw Jerald S. , Krakowiak Krzysztof E. , An Haoyun , Izatt Reed M. 
Published: March 2009

AbstractSeven new per(N‐formyl)polyaza‐crown macrocycles 1‐7 containing 14 to 21 ring members have been synthesized in yields of over 40% via the cyclization reaction of the appropriate per(N‐formyl)polyamine 11‐13 with the appropriate ditosylate, dibromide or diiodide. Three of the per(N‐formyl) macrocycles 5‐7 were hydrolyzed under acidic conditions to give the unsubstituted polyaza macrocycles 8‐10 in yields of over 77%.
Reactions of tetrasulfur tetranitride with bromomethyl ketones. One pot synthesis of 3,5‐diaroyl‐ and 3,5‐diacyl‐1,2,4‐thiadiazoles
Authors: Cho Jaeeock , Kim Kyongtae 
Published: March 2009

AbstractReactions of tetrasulfur tetranitride (S4N4) with aryl and alkyl bromomethyl ketones1in chlorobenzene at reflux temperature gave 3,5‐diaroyl‐ and 3,5‐diacyl‐1,2,4‐thiadiazoles2in 17‐60% yields. No 1,2,5‐thiadiazoles were detected. By heating of the two reactants at 115° without the solvent were also obtained2in 5‐13% yields. Hydrolysis of2with sodium hydroxide in a mixture of ethanol, ethyl acetate, and water (v:v, 4:2:1) at 75° to 85° afforded the heretofore inaccessible 3‐aroyl‐ and 3‐acyl‐1,2,4‐thiadiazoles3in 17‐79% yields.
New heterocyclic structures. [1,2,5]Thiadiazolo[3′,4′:4,5]pyrimido‐[2,1‐b][1,3]thiazine and thiazolo[3,2a][1,2,5]thiadiazolo[3,4‐d]pyrimidine
Authors: Pecorari Piergiorgio , Rinaldi Marcella , Costi M. Paola , Antolini Luciano 
Published: March 2009

AbstractDerivatives of two new molecular structures, namely, 7,8‐dihydro‐6H,10H‐[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1‐b][1,3]thiazin‐10‐one and 6,7‐dihydro‐9H‐thiazolo[3,2‐a][1,2,5]thiadiazolo[3,4‐d][pyrimidin‐9‐one, and derivatives of N‐substituted sulfamic acid, namely, (8‐amino‐3,4‐dihydro‐2H,6H‐pyrimido[2,1‐b][1,3]thiazin‐6‐on‐7‐yl)sulfamic acid and (7‐amino‐2,3‐dihydro‐5H‐thiazolo[3,2‐a]pyrimidin‐5‐on‐6‐yl)sulfamic acid, were separated out as by‐products in the reduction reaction of 8‐amino‐3,4‐dihydro‐7‐nitroso‐2H,6H‐pyrimido[2,1‐ b][1,3]thiazin‐6‐one and 7‐amino‐2,3‐dihydro‐6‐nitroso‐5H‐thiazolo[3,2‐a]pyrimidin‐5‐one derivatives, respectively, with sodium hydrosulfite.A mechanism of reaction, which hypothesizes the action of sodium hydrosulfite in an asymmetic form, is proposed.The results of single‐crystal X‐ray investigation on 7,8‐dihydro‐6H,10H‐[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1‐b][1,3]thiazin‐10‐one (R = 0.032 for 863 reflections) and (8‐amino‐3,4‐dihydro‐2H,6H‐pyrimido[2,1‐b]‐ [1,3]thiazin‐6‐on‐7‐yl)sulfamic acid, sodium salt (R = 0.028 for 3507 reflections) are reported.
The total synthesis of β‐lapachone
Authors: Amaral Aná Claudia F. , Barnes Roderick A. 
Published: March 2009

AbstractThe synthesis of β‐lapachone has been accomplished in eight steps with an overall yield of twenty‐three percent starting from alpha‐naphthol. The yields from the various steps were sufficiently good to insure that the derivatives of β‐lapachone which might be effective against Chagas' disease could be obtained in reasonable amounts.
Synthesis of the four stereoisomers of several 3‐(1‐aminoethyl)pyrrolidines. Important intermediates in the preparation of quinolone antibacterials
Authors: Schroeder Mel C. , Kiely John S. , Laborde Edgardo , Johnson Don R. , Szotek Deedee L. , Domagala John M. , Stickney Thomas M. , Michel Andre , Kampf Jeffrey W. 
Published: March 2009

AbstractThe use of S‐α‐methylbenzyl as a chiral auxiliary at N1 allowed separation of diastereomeric 2‐pyrrolidinones substituted with an ester, ketoester, ketone and oxime at the C4 position. Reduction of each diastereomer of 4‐[1‐(hydroxyimino)ethyl]‐1‐(1‐phenylethyl)‐2‐pyrrolidinone, 10s and 10r, provided a pair of epimeric amines, [11sr and 11ss] and [11rs and 11rr], that were separated by chromatography. The four stereoisomers of 4‐(1‐aminoethyl)‐1‐(1‐phenylethyl)‐2‐pyrrolidinone, 11, were elaborated into several stereochemically pure 3‐(1‐aminoethyl)pyrrolidines, 1 and 15‐23. These compounds are useful intermediates (C7 side chains) for quinolone antibacterials.
Synthesis of derivatives of pyrazolo[1,5‐a]pyrrolo[1,2‐c][1,3,6]‐benzotriazocine, a new class of compounds with potential CNS activity
Authors: Costanzo Annarella , Bruni Fabrizio , Guerrini Gabriella , Selleri Silvia , Aiello Petra Malmberg , Lamberti Claudia 
Published: March 2009

AbstractThe synthesis of derivatives of pyrazolo[1,5‐a]pyrrolo[1,2‐c][1,3,6]benzotriazocine was obtained by the reaction of arylaldehydes with some 1‐(2‐aminophenyl)‐5‐(pyrrol‐1‐yl)pyrazoles, as hydrochlorides. Characterization of this new class of compounds was effected with ir, pmr and13C nmr spectral data.
Synthesis and reactivity of furo[2,3‐e]pyrrolo[1,2‐a][1,4]diazepin‐9‐one
Authors: Povazanèc Frantisek , Decroix Bernard , Morel Jean 
Published: March 2009

AbstractA convenient method for the synthesis of furo[2,3‐e]pyrrolo[1,2‐a][1,4]diazepin‐9‐one is described. It has been C‐alkylated with amine (piperidine, morpholine, 4‐methylpiperazine) and N‐alkylated with alkyl halides (methyl iodide and benzyl chloride).
Syntheses of triazolo[6,7‐d]phthalide and triazolo[6,7‐d]dihydrocoumarin
Authors: Katritzky Alan R. , Ji Fu‐Bao , Fan Wei‐Qiang , Beretta Paolo , Bertoldi M. 
Published: March 2009

AbstractTriazolo[6,7‐d]phthalide has been synthesized in a seven step sequence from phthalide in 24% overall yield, and triazolo[6,7‐d]dihydrocoumarin has been prepared in nine steps from dihydrocoumarin in 20% overall yield. The 1H and 13C nmr spectra and the tautomeric equilibria of the final compounds and intermediates are discussed.
Synthesis of 3‐nitro‐ and 3‐aminoquinoline‐2,4‐diones. An unexpected route to 3‐hydroxyquinoline‐2,4‐diones
Authors: Stadlbauer Wolfgang , Lutschounig Herbert , Schindler Gerda , Witoszynskyj Theo , Kappe Thomas 
Published: March 2009

AbstractNitration of 3‐substituted‐4‐hydroxy‐2(1H)‐quinolones 1 with nitric acid leads either to 3‐nitro‐ 2 or 3‐hydroxyquinolinediones 3, depending on the reaction conditions. 3‐Substituted‐3‐hydroxyquinolinediones 3 are also obtained by oxidative hydroxylation with peracetic acid. Amination of 3‐substituted‐3‐chloroquinolinediones 4 with ammonium hydroxide predominantly leads again to 3‐substituted‐3‐hydroxyquinolinediones 3, only in one case the 3‐aminoquinolinedione 5 could be isolated. With morpholine or pyridine as amines the expected 3‐aminoquinolinediones 6 and 7 were obtained.
Synthesis and stereochemistry of (3α)‐6β,7β‐dihydroxy‐ and 6β‐hydroxy‐8‐alkyl‐8‐azabicyclo[3.2.1]octane‐3‐spiro‐5′‐imidazoline‐2′,4′‐diones
Authors: Villacampa Mercedes , Martínez Manuel , González‐Trigo Gregorio , Söllhuber Mó Nica M. 
Published: March 2009

AbstractThe synthesis of 6β‐hydroxy‐ and 6β,7β‐dihydroxy‐8‐alkyl‐8‐azabicyclo[3.2.1]octane‐3‐spiro‐5′‐hydantoins was stereoselectively achieved by Bucherer‐Bergs reaction of the corresponding ketones. An α configuration on C3 was proposed for all hydantoins on the basis of spectral data.
Synthesis of 6‐amino‐2‐aryl‐1,2‐dihydro‐3H‐pyrido[2,3‐d]pyrimidin‐4‐one derivatives
Authors: Monge A. , Martinez‐Merino V. , Simon M. A. , Sanmartin C. 
Published: March 2009

AbstractThis paper reports the synthesis of new pyrido[2,3‐d]pyrimidin‐4‐one derivatives as diuretic agents. Starting with 1,2‐dihydro‐5‐nitro‐2‐oxo‐3‐pyridinecarboxylic acid 1, ethyl 2‐ethoxy‐5‐nitro‐3‐pyridincarboxylate 4 was obtained. Compound 4 reacts with ammonia, methylamine or S‐methylpseudothiourea to give the respective 2‐amino‐5‐nitro‐3‐pyridinecarboxamide derivatives 5 and 6 or 2‐methylthio‐6‐nitro‐3H‐pyrido[2,3‐d]pyrimidin‐4‐one 8. Treating carboxamide 5 with arylaldehydes and zinc dichloride, new 2‐aryl‐1,2‐dihydro‐6‐nitro‐3H‐pyrido[2,3‐d]pyrimidin‐4‐ones 9 were synthetised. These compounds reduced with iron(II) hydroxide gave 6‐amino‐2‐aryl‐1,2‐dihydro‐3H‐pyrido[2,3‐d]pyrimidin‐4‐ones 10 as expected.
1‐Chloro‐2‐azapropenylium and 1‐chloro‐2,4‐diazabutenylium salts. Intermediates for the synthesis of pyrido[1,2‐a]‐1,3,5‐triazinium salts
Authors: Okide George Bosah 
Published: March 2009

Abstract1‐Chloro‐1,3‐bis(dimethylamino)‐3‐phenyl‐2‐azaprop‐2‐en‐1‐ylium perchlorate obtained from the reaction of phosphorus oxychloride‐N,N‐dimethylbenzamide complex and dimethylcyanamide reacts with 2‐amino‐4‐methylpyridine to yield 8‐methyl‐4‐dimethylamino‐2‐phenylpyrido[1,2‐a]‐1,3,5‐triazinium perchlorate (8). The structure is established by X‐ray crystallography. Various suitably substituted pyridines react similarly to afford the corresponding pyrido[1,2‐a]‐1,3,5‐triazinium salts. The intermediates obtained from several secondary amides give identical products when treated with the same pyridines. The limitations of this procedure are investigated.
Synthesis and photochemical degradation of N‐arylmethyl derivatives of the herbicide 3‐amino‐1,2,4‐triazole
Authors: Er‐Rhaimini Abderrahman , Mornet René 
Published: March 2009

AbstractReaction of an arylmethyl halide with 3‐amino‐1,2,4‐triazole (1) allows the preparation of the three N‐aryl‐methyl derivatives of 1 bearing the substituent on the heterocyclic nitrogen atoms. In basic medium (methoxide anion in DMF or methanol, or in benzene by phase transfer catalysis), the isomers 3 and 5 substituted at N‐1 and N‐2 respectively are obtained, while the isomer 4 is isolated from neutral medium (DMF). The isomers 3 and 4 may be also prepared by cyclization of appropriate formylguanidinium derivatives. 3‐Arylmethylamino‐1,2,4‐triazoles 2 may be obtained through reaction of 3‐chloro‐1,2,4‐triazole (6) with arylmethylamines. Photolysis of the N‐arylmethyl‐3‐amino‐1,2,4‐triazoles 2‐5 in methanol or water‐methanol mixture, induces homolytic and heterolytic cleavage of the arylmethyl‐C‐N bond giving rise to 3‐amino‐1,2,4‐triazole (1). Thus, compounds 2‐5 with arylmethyl groups able to absorb solar light may be considered as potential photoactivatable herbicides.
Alkylation of pyridine‐3,5‐dicarboxamide and pyridine‐3,5‐dicarbonitriles by radical substitution
Authors: Kanomata Nobuhiro , Nagahara Hisashi , Tada Masaru 
Published: March 2009

AbstractStructural modification of NAD(P) model compounds, N,N,N',N'‐tetramethylpyridine‐3,5‐dicarboxamide (1), pyridine‐3,5‐dicarbonitrile (2), and 4‐methylpyridine‐3,5‐dicarbonitrile (3), have been explored by the reaction with alkyl radicals such as the 1‐adamantyl, tert‐butyl, and isopropyl radicals. The alkyl substitutions of compounds 1, 2, and 3 with the 1‐adamantyl and the tert‐butyl radical gave both 2‐mono and 2,6‐disubstitution products, whereas the reaction of compound 2 with the isopropyl radical gave 2‐mono 6c, 2,4‐di 7c, 2,6‐di 8c, and 2,4,6‐trisubstitution 9c products.
α‐Pyrones. II. Synthesis of tetrahydroquinoline derivatives of 4‐aminobutanoic and 2‐amino‐2‐pentenedioic acids
Authors: Bombarda Carlo , Erba Emanuela , Gelmi Maria Luisa , Pocar Donato 
Published: March 2009

AbstractEthyl 3‐benzoylamino‐2‐oxo‐6‐triphenylphosphoranylidenemethyl‐2H‐pyran‐5‐carboxylate (1) reacts with 2‐ nitrobenzaldehydes (2) to give 6‐(2‐nitrostyryl)‐2H‐pyran‐2‐ones (3), as the E stereoisomers, in good yields. The reduction of compounds 3, performed with hydrogen over Pd/C at room temperature and 1 atmosphere, leads to a mixture of 2‐amino‐4‐tetrahydroquinolinylidene‐2‐pentenedioic acid derivatives 5a‐d as the main products, the corresponding 3‐butenoic acid derivatives 6 and a minor amount of pyrano[2,3‐c]benzazocines 9a‐c. At 40 atmospheres and 90°, the reduction gives 4‐amino‐2‐tetrahydroquinolinylbutanoic acid derivatives 8a‐d as the main products and their precursors 7a,b,d as the minor ones. Amines 4c,d are isolated by stopping the reduction after the uptake of 3 equivalents of hydrogen.
Methyl imidazo[1,2‐b]pyridazine‐2‐carbamates and related compounds as potential antifilarial agents
Authors: Mourad Alaa E. , Wise Dean S. , Townsend Leroy B. 
Published: March 2009

AbstractA series of imidazo[1,2‐b]pyridazines have been synthesized for antifilarial evaluation. The compounds prepared include methyl 6‐benzoylimidazo[1,2‐b]pyridazine‐2‐carbamate (12), 6‐benzoyl‐2‐t‐butylimidazo[1,2‐b]pyridazine (13), methyl 6‐(4‐fluorobenzoyl)imidazo[1,2‐b]pyridazine‐2‐carbamate (14), and methyl 6‐(2‐thienylcarbonylcarbonyl)imidazo[1,2‐b]pyridazine‐2‐carbamate (15) which are aza analogs of the anthelmintic agents mebendazole, flubendazole and nocadazole. In addition, the preparation of a series of 2‐t‐butylimidazo[1,2‐b]‐pyridazine‐6‐carboxylic acid derivatives is described. Electrophilic bromination and iodination substitutions of 2‐t‐butyl‐6‐methylimidazo[1,2‐b]pyridazine afforded 3‐halo derivatives. Methyl 6‐(4‐fluorobenzoyl)pyridazine‐3‐carbamate was also prepared for antifilarial evaluation. None of these compounds possessed significant antifilarial activity against Brugia pahangi or Acanthocheilonema viteae infections in jirds.
4,5‐Dihydroisoxazole and 4,5‐dihydro‐1,2,4‐oxadiazole derivatives from cycloaddition reactions of nitrile oxides to alkyl N‐(diphenylmethylene)‐α,β‐dehydroamino acids
Authors: Balsamini Cesarino , Spadoni Gilberto , Bedini Annalida , Tarzia Giorgio , Lanfranchi Maurizio , Pellinghelli Maria Angela 
Published: March 2009

AbstractThe alkyl N‐(diphenylmethylene)‐α,β‐dehydroamino acids 1 have been submitted to 1,3‐dipolar cycloadditions with nitrile oxides. The reactivity of these compounds depends on the type and on the stereochemistry of the β‐substituents. With the unsubstituted terms 1a,b the reaction occurs on the C,C double bond, providing a good method for the synthesis of the 4,5‐dihydroisoxazole derivatives 3a,b,c and for the gem‐functionalized 4,5‐dihydroisoxazoles amino carboxylic ester 5. The β‐substituted compounds 1c,d,e, inert to 1,1‐dimethylethylnitrile oxide, undergo the reaction to the N,C double bond, thus giving with 2a,b the 4,5‐dihydro‐1,2,4‐oxadiazole derivatives 4. All the reactions occur with high site‐ and regioselectivity.
Reactions of thioquinanthrene with sodium alkanethiolates. The smiles rearrangement of diquinolinyl sulfides
Authors: Pluta Krystian 
Published: March 2009

AbstractReactions of thioquinanthrene 1 with sodium alkanethiolates or S‐alkylisothiouronium salts (in the presence of sodium hydroxide) at 70° in DMSO or DMF yielded 4,4′‐dialkylthio‐3,3′‐diquinolinyl sulfides 3, which were results of the S‐S type of the Smiles rearrangement of primary reaction products ‐ sodium 3‐quinoline‐thiolates 6. When the reactions were carried out at 20° the products were 3′,4‐dialkylthio‐3,4′‐diquinolinyl sulfides 2.
A novel synthesis of methyl cis‐(3‐thienyl)glycidate with 2‐aminothiophenol and the synthesis of [1,5]benzothiazepine derivatives
Authors: Lancelot Jean Charles , Letois Bertrand , Rault Sylvain , Saturnino Carmela , Robba Max , De Caprariis Paolo 
Published: March 2009

AbstractThe synthesis of cis‐2,3‐dihydro‐3‐hydroxy‐2‐(3‐thienyl)[1,5]benzothiazepin‐4(5H)‐one derivatives is described starting from 2‐aminothiophenol and methyl cis‐(3‐thienyl)glycidate. The structures were confirmed by 1H‐nmr spectroscopy.
Electrophilic acetylation and bromination reactions of benzo[b]naphtho[2,3‐e][1,4]dioxin
Authors: Piórko Adam , Crook Michelle , Sampson Peter 
Published: March 2009

AbstractThe reactivity of benzo[b]naphtho[2,3‐e][1,4]dioxin in the electrophilic aromatic substitution reactions has been studied. Friedel‐Crafts acetylation resulted in the formation of three out of the possible five monoacetylated products, with the acetyl group located in positions 8 (major), 7 and 6 (minor) of the heterocycle. In the bromination reaction a higher selectivity was observed with the 6‐bromo derivative found as the only monobrominated product and the 6,11‐dibromo derivative found as the only polybrominated product. A ratio of unreacted heterocycle:6‐bromo:6,11‐dibromo derivatives in the bromination reaction has been found to depend strongly on the reaction conditions and on the heterocycle:bromine ratio.