Efficient construction of 1,2-dihydroquinoline and 1,2,3,4-tetrahydroquinoline rings using tandem Michael-aldol reaction

被引：49
|
作者：
Makino, K
Hara, O
Takiguchi, Y
Katano, T
Asakawa, Y
Hatano, K
Hamada, Y [1 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
[2] Meijo Univ, Fac Pharm, Tempaku Ku, Nagoya, Aichi 4608503, Japan
[3] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 50期
关键词：
1,2-dihydroquinoline; 1,2,3,4-tetrahydroquinoline; tandem Michael-aidol reaction;
D O I：
10.1016/j.tetlet.2003.10.011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,2-Dihydroquinolines and a 1,2,3,4-tetrahydroquinoline were efficiently constructed using tandem Michael-aldol reaction starting from N-protected o-aminobenzaldehydes and alpha,beta-unsaturated carbonyl compounds in good yield. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8925 / 8929
页数：5
相关论文
共 50 条
  • [31] 1-(3-DIETHYLAMINO-1-PROPYL)-6-METHOXY-1,2,3,4-TETRAHYDROQUINOLINE
    MCKEE, RL
    MCKEE, MK
    BOST, RW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (02) : 471 - 471
  • [32] SYNTHESIS AND POSITIVE INOTROPIC EFFECT OF 1-ALKYL-6,7-DIMETHOXY-3-DIMETHYLAMINO-1,2,3,4-TETRAHYDROQUINOLINE AND 1-ACYL-6,7-DIMETHOXY-3-DIMETHYLAMINO-1,2,3,4-TETRAHYDROQUINOLINE
    SANTANGELO, F
    CASAGRANDE, C
    MIRAGOLI, G
    VECCHIETTI, V
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (11) : 877 - 882
  • [33] MECHANISM OF C-N BOND SCISSION - HYDRODENITROGENATION OF 1,2,3,4-TETRAHYDROQUINOLINE AND OF 1,2,3,4-TETRAHYDROISOQUINOLINE
    VIVIER, L
    DOMINGUEZ, V
    PEROT, G
    KASZTELAN, S
    JOURNAL OF MOLECULAR CATALYSIS, 1991, 67 (02): : 267 - 275
  • [34] IONIC STRUCTURE OF 1-METHYL-2-(3-INDOLYL)-1,2-DIHYDROQUINOLINE
    NEZDIYMINOGA, TN
    CHMILENKO, TS
    SHEINKMAN, AK
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1984, (03): : 418 - 419
  • [35] Indium-mediated domino reaction of nitroarenes with 2,3-dihydrofuran in water: An efficient synthesis of 1,2,3,4-tetrahydroquinoline derivatives
    Chen, L
    Li, ZG
    Li, CJ
    SYNLETT, 2003, (05) : 732 - 734
  • [36] Heterogeneous Synergistic Catalysis for Promoting Aza-Michael-Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline
    An, Zhe
    Chen, Lifeng
    Jiang, Yitao
    He, Jing
    CATALYSTS, 2019, 9 (09)
  • [37] Efficient cyclization of ω-oxo-α,β-unsaturated esters using lithium thiolate-initiated Michael-aldol tandem reaction
    Ono, M
    Nishimura, K
    Nagaoka, Y
    Tomioka, K
    TETRAHEDRON LETTERS, 1999, 40 (38) : 6979 - 6982
  • [38] Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation
    Manolov, Stanimir
    Ivanov, Iliyan
    Bojilov, Dimitar
    MOLBANK, 2022, 2022 (01)
  • [39] Crystal structure of 1-[(6-chloropyridin-3-yl) sulfonyl]-1,2,3,4-tetrahydroquinoline
    Jeyaseelan, S.
    Rajegowda, H. R.
    Rayan, R. Britto Dominic
    Kumar, P. Raghavendra
    Palakshamurthy, B. S.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : 660 - +
  • [40] FLUORESCENCE CHARACTERISTIC AND MOLECULAR INTERACTION IN THE EXCITED-STATE OF 1,2,3,4-TETRAHYDROQUINOLINE
    CHATTERJEE, K
    LAHA, S
    CHAKRAVORTI, S
    GANGULY, T
    BANERJEE, SB
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07): : 1369 - 1372
12345