Thermal cyclization of 3-arylamino-3-(2-nitrophenyl)-propenal Schiff base hydrochlorides followed by triethyl phosphite mediated deoxygenation: a facile synthesis of quindolines

被引:25
作者
Dutta, B [1 ]
Some, S [1 ]
Ray, JK [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
quindoline; cryptolepine;
D O I
10.1016/j.tetlet.2005.11.007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and useful method for the synthesis of various 2-substituted quindolines starting from 2-nitroacetophenone is described. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:377 / 379
页数:3
相关论文
共 19 条
  • [1] Probing the N-5 region of the indoloquinoline alkaloid, cryptolepine for anticryptococcal activity
    Ablordeppey, SY
    Fan, PC
    Clark, AM
    Nimrod, A
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) : 343 - 349
  • [2] [Anonymous], 1983, P 1 INT SEMINAR CRYP
  • [3] New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines
    Arzel, E
    Rocca, P
    Grellier, P
    Labaeïd, M
    Frappier, F
    Guéritte, F
    Gaspard, C
    Marsais, F
    Godard, A
    Quéguiner, G
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) : 949 - 960
  • [4] Antihyperglycemic activities of cryptolepine analogues:: An ethnobotanical lead structure isolated from Cryptolepis sanguinolenta
    Bierer, DE
    Dubenko, LG
    Zhang, PS
    Lu, Q
    Imbach, PA
    Garofalo, AW
    Phuan, PW
    Fort, DM
    Litvak, J
    Gerber, RE
    Sloan, B
    Luo, J
    Cooper, R
    Reaven, GM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (15) : 2754 - 2764
  • [5] Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities
    Bierer, DE
    Fort, DM
    Mendez, CD
    Luo, J
    Imbach, PA
    Dubenko, LG
    Jolad, SD
    Gerber, RE
    Litvak, J
    Lu, Q
    Zhang, PS
    Reed, MJ
    Waldeck, N
    Bruening, RC
    Noamesi, BK
    Hector, RF
    Carlson, TJ
    King, SR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) : 894 - 901
  • [6] Synthesis of substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides:: Evaluation of structure-activity relationships for cytotoxicity
    Chen, JJ
    Deady, LW
    Desneves, J
    Kaye, AJ
    Finlay, GJ
    Baguley, BC
    Denny, WA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (10) : 2461 - 2466
  • [7] In vitro biological activities of alkaloids from Cryptolepis sanguinolenta
    Cimanga, K
    DeBruyne, T
    Lasure, A
    VanPoel, B
    Pieters, L
    Claeys, M
    VandenBerghe, D
    Kambu, K
    Tona, L
    Vlietinck, AJ
    [J]. PLANTA MEDICA, 1996, 62 (01) : 22 - 27
  • [8] Indole-beta-nucleophilic substitution .9. Nitrogen nucleophiles. Syntheses of hydroxycryptolepine, cryptolepine, and quindoline
    Cooper, MM
    Lovell, JM
    Joule, JA
    [J]. TETRAHEDRON LETTERS, 1996, 37 (24) : 4283 - 4286
  • [9] FEIJAO RO, 1961, ELUCIDARIO FITOLOGIC, V2, P258
  • [10] Fichter F, 1906, CHEM BER, V39, P3932