Novel and convenient synthesis of polyfunctionalized quinolines, quinolones and their annulation reactions

被引：48
|
作者：
Wang, MX [1 ]
Liu, Y [1 ]
Huang, ZT [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 13期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/S0040-4039(01)00231-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of alpha -aroylketene dithioacetals with esters of o-aminobenzoic acid under different conditions afforded preferentially 2-methylthio-3-aroylquinolones and 2-anilino-3-aroylquinolines through, respectively, alpha -aroylketene N,S-acetal and alpha -aroylketene aminal intermediates. The annulation reaction of 2-methylthio-3-aroylquinolones with hydrazine gave both pyrazolo[3,4-b]quinolone and pyrazolo[4,3-c]quinoline, the selectivity being determined by the reaction conditions employed. Intramolecular cyclocondensation of 2-anilino-3-aroylquinolines produced quino[2,1-b]quinazolines in high yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2553 / 2555
页数：3
相关论文
共 50 条
  • [21] Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions
    Babu, G
    Perumal, PT
    TETRAHEDRON LETTERS, 1998, 39 (20) : 3225 - 3228
  • [22] Synthesis of Quinolines via Rh(III)-Catalyzed Oxidative Annulation of Pyridines
    Song, Guoyong
    Gong, Xue
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18): : 7583 - 7589
  • [23] A CONVENIENT SYNTHESIS OF 3-(4-PYRIDINYL)QUINOLINES
    SINGH, B
    LESHER, GY
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (05) : 1453 - 1454
  • [24] A CONVENIENT SYNTHESIS OF PYRANO (2,3-b) QUINOLINES
    Shankar, K.
    Rajendran, S. P.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 19 (04) : 407 - 408
  • [25] A convenient synthesis of pyrrolo[3,4-c]quinolines
    Nyerges, N
    Virányi, A
    Töke, L
    HETEROCYCLIC COMMUNICATIONS, 2003, 9 (03) : 239 - 242
  • [26] A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation-methoxylation reactions of selenium dihalides
    Musalov, Maxim V.
    Yakimov, Vladimir A.
    Potapov, Vladimir A.
    Amosova, Svetlana V.
    Borodina, Tatyana N.
    Zinchenko, Sergey V.
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (47) : 18476 - 18483
  • [27] A convenient synthesis of pyrrolo[3,4-c]quinolines
    Virányi, A
    Nyerges, M
    Blaskó, G
    Töke, L
    SYNTHESIS-STUTTGART, 2003, (17): : 2655 - 2660
  • [28] Synthesis of polyfunctionalized pyrido[1,2-a]pyrazines and pyrazino[1,2-a]quinolines via one-pot multicomponent reactions
    Renata I. Eften’eva
    Oleg V. Kushnir
    Oleksandr S. Lyavinets
    Ionel I. Mangalagiu
    Myhailo V. Vovk
    Monatshefte für Chemie - Chemical Monthly, 2016, 147 : 2127 - 2133
  • [29] Synthesis of polyfunctionalized pyrido[1,2-a]pyrazines and pyrazino[1,2-a]quinolines via one-pot multicomponent reactions
    Eften'eva, Renata I.
    Kushnir, Oleg V.
    Lyavinets, Oleksandr S.
    Mangalagiu, Ionel I.
    Vovk, Myhailo V.
    MONATSHEFTE FUR CHEMIE, 2016, 147 (12): : 2127 - 2133
  • [30] TRIALKYLSILYLOXYALKYNES - SYNTHESIS AND AROMATIC ANNULATION REACTIONS
    DANHEISER, RL
    NISHIDA, A
    SAVARIAR, S
    TROVA, MP
    TETRAHEDRON LETTERS, 1988, 29 (39) : 4917 - 4920
12345