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
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
收藏
页码:2261 / 2265
页数:5
相关论文
共 58 条
  • [1] Substituted indoloquinolines as new antifungal agents
    Ablordeppey, SY
    Fan, PC
    Li, SM
    Clark, AM
    Hufford, CD
    [J]. 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
    Amii, H
    Kishikawa, Y
    Uneyama, K
    [J]. 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
    Arcadi, A
    Marinelli, F
    Rossi, E
    [J]. 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
    Arisawa, M
    Terada, Y
    Theeraladanon, C
    Takahashi, K
    Nakagawa, M
    Nishida, A
    [J]. 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
    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
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (23) : 7468 - 7476
  • [8] Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito
    Billker, O
    Lindo, V
    Panico, M
    Etienne, AE
    Paxton, T
    Dell, A
    Rogers, M
    Sinden, RE
    Morris, HR
    [J]. NATURE, 1998, 392 (6673) : 289 - 292
  • [9] Synthesis and antibacterial evaluation of certain quinolone derivatives
    Chen, YL
    Fang, KC
    Sheu, JY
    Hsu, SL
    Tzeng, CC
    [J]. 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
    Chevalier, J
    Atifi, S
    Eyraud, A
    Mahamoud, A
    Barbe, J
    Pagès, JM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) : 4023 - 4026