Synthesis of 4-Hydroxy- and 4-Amino-2-Methyl-3-(2-Methylindol-3-Yl)methylquinolines and Their 6- and 8-Substituted Derivatives

A method has been developed for the synthesis of substituted 4-hydroxy- and 4-amino-2-methyl-3-(2-methylindol-3-yl)methylquinolines by treating the corresponding 4-hydroxy(chloro)-2-methyl-3-(3-oxobutyl)quinolines with phenylhydrazine hydrochloride. It was found that nucleophilic substitution occurred in the case of the 4-chloroquinolines together with subsequent rearrangement to give the 4-amino derivatives. The thiosemicarbazones of the corresponding 4-hydroxy-2-methyl-3-(3-oxobutyl)quinolines were also obtained.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 554–557, April, 2005.     

4-Hydroxy-2-quinolones. 56. 4-(Adamant-1-yl)thiazolyl-2-amides of 1-R-4-Hydroxy-2-oxoquinoline-3-carboxylic Acids as Potential Antitubercular Agents

The synthesis, antitubercular, anti-HIV, and antitumor activity of the 4-(adamant-1-yl)thiazolyl-2-amides of 1-R-4-hydroxy-2-oxoquinoline-3-carboxylic acids have been studied. An efficient method for purifying the 4-hydroxy-2-oxoquinoline derivatives from their metal salts is proposed.     

~(18)F标记前体3'-甲氧基-7-对甲苯磺酰氧丙氧基槲皮素的合成

以槲皮素为起始原料,经酰化、醚化、苄醚化、脱苄、甲基化、水解6步反应合成了18F标记前体3'-甲氧基-7-对甲苯磺酰氧丙氧基槲皮素,其结构经1H NMR,13C NMR和HR-MS(ESI)确证。     

Synthesis of 3-alkylamino-3-(2-hydroxyaryl)-1-polyfluoroalkylprop-2-en-1-ones and 2-polyfluoroalkyl-4H-chromen-4-imines

Condensation of Schiff"s bases (prepared from 2-hydroxy- or 2-hydroxy-5-methylacetophenones and primary amines) with ethyl polyfluoroalkanoates in the presence of LiH in THF affords 3-alkylamino-3-(2-hydroxyaryl)-1-polyfluoroalkylprop-2-en-1-ones, which undergo cyclization in acidic media into 2-polyfluoroalkyl-4H-chromen-4-iminium salts. When neutralized with aqueous ammonia, the latter give 2-polyfluoroalkyl-4H-chromen-4-imines in high yields.     

Synthesis of 5-Substituted-3-[(2’R,4’R)-4’-Hydroxy-2’-hydroxymethyltetrahydrofuran-4’-yl]-1,2,4-oxadiazoles and Their Epimers

The syntheses of 5-substituted-3-[( 2' R, 4' R)-4 ' -hydroxy-2 ' -hydroxymethyltetra-hydrofuran-4' -yl]D-1 ,2, 4-oxadiazoles and their epimers were accomplished with the aid of th construction of 1,2, 4-oxadiazoles by condensation of O-acylated cyanohydrins with hydroxylamine via intramolecular transacylation and subsequent cyclization.     

Novel,Simple, and Efficient Synthesis of 3-(2-(5-(Benzylideneamino)-3-phenyl-1H-pyrazol-1-yl)thiazol-4-yl)-4-hydroxy-6-methyl-2H-pyran-2-one Derivatives via a One-Pot,Four-Component Condensation Reaction

The synthesis of 3-(2-(5-(benzylideneamino)-3-phenyl-1H-pyrazol-1-yl)thiazol-4-yl)-4-hydroxy-6-methyl-2H-pyran-2-one derivatives was achieved through a one-pot, four-component reaction involving condensation of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiosemicarbazide, phenacylcyanaide, and various aryl aldehydes in dry alcohol and few drops of acetic acid under reflux condition. This four-component reaction has some advantages such as ease of handling, good yields, and easy workup. All structures of newly prepared compounds were confirmed by analytical and spectral data.     

2－氯／2－甲磺酰基－5－（2－苯基－4－喹啉基）－1，3，4－噁二唑化合物的合成及其亲核取代的研究

借处理２－羟基－５－（２－苯基－４－喹啉基）－１，３，二唑同ＰＣｌ＿５／ＰＯＣｌ＿３之间的反应合成了２－氯－５－（２－苯基－４－喹啉基）－１，３，４－二唑（３）和通过２－基－５－（２－苯基－４－喹啉基）－１，３，４－二唑的甲基化，然后氧化制得２－甲磺酰基－５－（２－苯基－４－喹啉基）－１，３，４－二唑（６）．并分别研究了３和６同胺、叠氮及肼的反应，得到２，５－二取代的二唑新衍生物．初步观察了部分化合物的抗菌活性．     

2-[2-(4, 6-二甲基)-嘧啶基]-4-苯基-1, 2, 4-恶二唑烷-3, 5-二酮的合成

异氰酸苯酯和N-[2-(4, 6-二甲基)-嘧啶基]-羟胺(5)反应生成1-[2-(4, 6-二甲基)-嘧啶基]-1-羟基-3-苯基脲(6)。化合物(6)在三乙胺存在下和氯甲酸乙酯反应生成2-[2-(4, 6-二甲基)-嘧啶基]-4-苯基-1, 2, 4-恶二唑烷-3, 5-二酮(1)。     

Synthesis of Derivatives of 4-Hydroxy-2-methyl-3-[2-(5-mercapto-1H-1,2,4-triazol-3-yl)ethyl]quinoline and 2-[2-(4-Hydroxy-2-methyl-3-quinolyl)ethyl]-4H-3,1-benzoxazin-4-one

From 4-hydroxy-2-methylquinoline-3-propionyl chlorides hydrochlorides the corresponding thiosemicarbazides were synthesized. The cyclization of the latter both in alkaline and acidic media furnished 4-hydroxy-2-methyl-3-[2-(5-mercapto-1H-1,2,4-triazol-3-yl)ethyl]quinolines. The reaction of the above propionyl chlorides with anthranilic acid afforded the corresponding 2-[2-(4-hydroxy-2-methyl-3-quinolyl)ethyl]-4H-3,1-benzoxazin-4-ones.     

Synthesis of 2-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-carbonyl)-6,6-dimethyl-3-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one Derivatives via Multicomponent Reaction

A sequential one-pot, two-step reaction for an efficient preparation of 2-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-carbonyl)-6,6-dimethyl-3-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one derivatives has been described. One-pot reaction of in situ–formed benzopyran-substituted pyridinium ylides with aromatic aldehydes and dimedone gives corresponding 2,3-dihydrofurans in good yields. The structures of all the newly synthesized compounds were confirmed from their analytical and spectral data.     

4-Hydroxy-2-quinolones. 152*. 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline and its biologically active derivatives

A synthesis and study of the spatial structure of 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline have been carried. 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids [1-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)ethylidene]hydrazides were prepared from this compound by two routes. A comparative analysis of the antitubercular properties of the synthesized compounds and of the closely structurally related N,N′-di(1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)hydrazines has been performed. *For Communication 151 see [1]. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–222, February, 2009.     

Synthesis and Alkylation of 4-(2-Chlorophenyl)-3-cyano-6-hydroxy-5-(2-thienoyl)-6-trifluoromethylpiperidin-2-thione

4-(2-Chlorophenyl)-3-cyano-6-hydroxy-5-(2-thienoyl)-6-trifluoromethylpiperidin-2-thione, which was used for the synthesis of 2-allylthio-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thienoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine, was obtained by the reaction of 2-thienoyltrifluoroacetone with 2-chlorophenylphenylmethylenecyanothioacetamide or with a mixture of 2-chlorobenzaldehyde and cyanothioacetamide in the presence of N-methylmorpholine. The molecular and crystal structure of the piperidinthione have been established by X-ray crystallography.     

2-[4-(2,6-二氟苯基)噻唑-2-基]-3-羟基丙烯腈衍生物的合成及生物活性

为了寻找生物活性良好的噻唑基丙烯腈类化合物, 利用2-[4-(2,6-二氟苯基)噻唑-2-基]乙腈(3)分别与取代氯甲酸酯4和取代苯基异氰酸酯6在碱存在下反应, 合成了8个2-[4-(2,6-二氟苯基)噻唑-2-基]-3-羟基-3-烃氧基丙烯腈化合物5和7个2-[4-(2,6-二氟苯基)噻唑-2-基]-3-羟基-3-取代苯胺基丙烯腈化合物7, 均为首次报道的丙烯腈类化合物. 化合物结构经1H NMR, IR, MS和元素分析表征. 初步生物活性测定结果表明, 在试验浓度下, 目标化合物均具有一定的杀虫和抑菌活性, 其中化合物5f和5h在100 mg/L浓度下对炭疽病菌的抑制率达95%; 化合物5g和7d在250 mg/L浓度下对棉红蜘蛛的致死率达85%.     

Synthesis and Antimicrobial Activity of 3-(1-Aryl-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)propan-1-ones

Russian Journal of General Chemistry - A number of novel 3-(1-aryl-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl) propan-1-ones has been synthesized from...     

Synthesis of Gingerenone C and 5-Hydroxy-1-(4'-hydroxy- 3'-methoxyphenyl)-7-(4"-hydroxyphenyl)-3-heptanone

The two diarylheptanoids (E)-1-(4'-hydroxy-3'-methoxyphenyl)-7-(4"-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-7-(4"-hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.     

Synthesis, structure, and properties of piperidinium 3-(4-chlorophenyl)-2-cyano-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)thiopropionimidate

Condensation of 4-chlorobenzaldehyde with cyanothioacetamide and dimedone in the presence of piperidine afforded piperidinium 3-(4-chlorophenyl)-2-cyano-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)thiopropionimidate. This salt was studied by X-ray diffraction analysis and used in the synthesis of the previously unknown partially hydrogenated 2-alkylthioquinolin-2-ones. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 733–737, April, 2000.     

A convenient synthesis of methyl 2-hydroxy-4-oxo-4-(substituted phenyl) butanoates from malic acid

A synthesis of methyl 2-hydroxy-4-oxo-4-(substituted phenyl)butanoates has been accomplished using Friedel-Crafts acylation of substituted benzenes with 2-acetoxybutanoyl chloride.The key feature of this strategy is that various 4-arylbutanoates can be obtained conveniently,which are important intermediates for the synthesis of biologically active compounds including ACE inhibitors.     

3-烷基/芳基-6-(2', 4'-二氯苯基)-7H-1, 2, 4-三唑[3, 4-b]- 1, 3, 4-噻二 嗪的合成及波谱性质

以间二氯苯与氯乙酰氯反应,生成ω-氯代-2,4-二氯苯乙酮(1),再使之分别与3-烷基/芳基-4-氨基-5-巯基-1,2,4-三唑(2a～2l)反应,合成了12种新的3-烷基/芳基-6-(2',4'-二氯苯基)-7H-1,2,4-三唑并[3,4-b]1,3,4-噻二嗪(4a～4l)。利用EA,IR,^1HNMR确定了其结构,并提出该反应的可能机制。     

Enantiomeric separation of novel anticancer agent 5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one

The enantiomers of 5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one, a novel anticancer agent, were separated by derivatisation with caronaldehyde, separation of the resulting diastereoisomers of the corresponding esters by silica gel column chromatography and regeneration of alcohols (S)-5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one and (R)-5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one under aqueous conditions. The absolute configuration of the enantiomers was determined by 1H NMR studies of the corresponding Mosher esters. Alternatively, the enantiomers were separated by preparative HPLC to collect the (S)- and (R)-5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-ones with high purity which was comparable with that obtained by the chemical method. The details of these methods have been presented herein.     

Silica Gel Catalyzed Stereoselective Conversion of Dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to Dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in Solvent-Free Conditions

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 1-hydroxy-2-acetonaphthone leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates. Silica gel was found to catalyze conversion of dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in solvent-free conditions at 90°;C in fairly good yields.