Triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides: a concise synthesis of glycocitlone alkaloids

被引：18
作者：
Kobayashi, Yusuke [1 ]
Harayama, Takashi [1 ]
机构：
[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Kanagawa 7692193, Japan
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 48期
基金：
日本学术振兴会;
关键词：
ONE-POT SYNTHESIS; DIVERSITY-ORIENTED SYNTHESIS; MULTICOMPONENT REACTIONS; VILSMEIER REAGENTS; FUSED PYRIDINES; QUINOLINES; CYCLIZATION; DERIVATIVES; INHIBITORS; EFFICIENT;
D O I：
10.1016/j.tetlet.2009.09.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method is presented for the concise synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones through triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides. This tandem process was successfully used for the rapid syntheses of glycocitlones A and C. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6665 / 6667
页数：3
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  • [1] Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX
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  • [2] 4-cyano-6,7-dimethoxycarbostyrils with solvent- and pH-independent high fluorescence quantum yields and emission maxima
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    Prokopcova, Hana
    Sefcovicova, Jana
    Steinschifter, Waltraud
    Taeubl, Anna E.
    Uray, Georg
    Stadlbauer, Wolfgang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) : 563 - 571
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    Selvi, S
    Balasubramanian, K
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  • [4] Ali MM, 2001, SYNLETT, P251
  • [5] A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions
    Amaresh, RR
    Perumal, PT
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    Rodriguez, Felix
    Fananas, Francisco J.
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    Boyd, Derek R.
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    Loke, Pui L.
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  • [8] Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramofecular domino hetero Diels-Alder reactions of 1-oxa-1,3-butadienes in aqueous medium
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  • [9] A planning strategy for diversity-oriented synthesis
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    Schreiber, SL
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  • [10] Unambiguous structure elucidation of the reaction products of 3-acyl-4-methoxy-1-methylquinolinones with hydroxylamine via NMR spectroscopy
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    Matteucci, Alessandra
    [J]. TETRAHEDRON, 2007, 63 (47) : 11656 - 11660
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