Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl)anilines with arylaldehydes in alcoholic solvents: an efficient one-pot synthesis of 4-alkoxy-2-arylquinolines

被引：32

作者：

Wang, Yong ^{[1
]}

Peng, Changlan ^{[1
]}

Liu, Lanying ^{[1
]}

Zhao, Jiaji ^{[1
]}

Su, Li ^{[1
]}

Zhu, Qiang ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Biol Chem, Guangzhou Inst Biomed & Hlth, Guangzhou 510663, Guangdong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 19期

关键词：

INDIRECT FRIEDLANDER SYNTHESIS; SUBSTITUTED QUINOLINES; 2,4-DISUBSTITUTED QUINOLINES; OXIDATIVE CYCLIZATION; RECENT PROGRESS; IN-VITRO; DERIVATIVES; 2-ARYL-1,2,3,4-TETRAHYDRO-4-QUINOLONES; 2-ARYLQUINOLINE; ANTIBACTERIAL;

D O I：

10.1016/j.tetlet.2009.02.206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of 4-alkoxy-2-arylquinolines has been developed. The reaction proceeds smoothly by heating a mixture of easily accessible 2-(2-(trimethylsilyl) ethynyl)anilines and arylaldehydes in alcoholic solvents in the presence of sulfuric acid. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2261 / 2265

页数：5

共 58 条

[1] Substituted indoloquinolines as new antifungal agents [J].

Ablordeppey, SY ;

Fan, PC ;

Li, SM ;

Clark, AM ;

Hufford, CD .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (05) :1337-1346

[2] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines [J].

Amii, H ;

Kishikawa, Y ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (08) :1109-1112

[3]

[Anonymous], 2005, SCI PHARM

[4] Synthesis of functionalised quinolines through tandem addition/annulation reactions of β-(2-aminophenyl)-α,β-ynones [J].

Arcadi, A ;

Marinelli, F ;

Rossi, E .

TETRAHEDRON, 1999, 55 (46) :13233-13250

[5] Development of novel reactions using ruthenium carbene catalyst and its application to novel methods for preparing nitrogen-containing heterocycles [J].

Arisawa, M ;

Terada, Y ;

Theeraladanon, C ;

Takahashi, K ;

Nakagawa, M ;

Nishida, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5398-5406

[6]

Bailly C, 2000, ANTI-CANCER DRUG DES, V15, P191

[7] Identification of borinic esters as inhibitors of bacterial cell growth and bacterial methyltransferases, CcrM and MenH [J].

Benkovic, SJ ;

Baker, SJ ;

Alley, MRK ;

Woo, YH ;

Zhang, YK ;

Akama, T ;

Mao, WM ;

Baboval, J ;

Rajagopalan, PTR ;

Wall, M ;

Kahng, LS ;

Tavassoli, A ;

Shapiro, L .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (23) :7468-7476

[8] Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito [J].

Billker, O ;

Lindo, V ;

Panico, M ;

Etienne, AE ;

Paxton, T ;

Dell, A ;

Rogers, M ;

Sinden, RE ;

Morris, HR .

NATURE, 1998, 392 (6673) :289-292

[9] Synthesis and antibacterial evaluation of certain quinolone derivatives [J].

Chen, YL ;

Fang, KC ;

Sheu, JY ;

Hsu, SL ;

Tzeng, CC .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377

[10] New pyridoquinoline derivatives as potential inhibitors of the fluoroquinolone efflux pump in resistant Enterobacter aerogenes strains [J].

Chevalier, J ;

Atifi, S ;

Eyraud, A ;

Mahamoud, A ;

Barbe, J ;

Pagès, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) :4023-4026

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