A convenient synthesis of 2-substituted indoles by the reaction of 2-(chloromethyl)phenyl isocyanides with organolithiums

被引：20
|
作者：
Kobayashi, Kazuhiro [1 ]
Iitsuka, Daisuke [1 ]
Fukamachi, Shuhei [1 ]
Konishi, Hisatoshi [1 ]
机构：
[1] Tottori Univ, Div Appl Chem, Dept Chem & Biotechnol, Grad Sch Engn, Tottori 6808552, Japan
来源：
TETRAHEDRON | 2009年 / 65卷 / 36期
关键词：
Indoles; Isocyanides; Organolithiums; Intramolecular substitution; Imidoyl anion; CYCLIZATION REACTIONS; 2,4-DISUBSTITUTED QUINOLINES; FUNCTIONALIZED ISOCYANIDES; EFFICIENT SYNTHESIS; DERIVATIVES; INDOLIZATION; FLUORIDE; LIGANDS; ALKYNES;
D O I：
10.1016/j.tet.2009.06.127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 2-(chloromethyl)phenyl isocyanides, readily available by dehydration of the respective N-[2-(chloromethyl)phenyl]formamides, with organolithiums produced 2-substituted indoles in satisfactory yields through addition of organolithiums to the isocyano carbon followed by intramolecular substitution reaction of the resulting imidoyl anion intermediates. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7523 / 7526
页数：4
相关论文
共 50 条
  • [31] A convenient one-pot synthesis of 2-substituted benzimidazoles
    Trivedi, R
    De, SK
    Gibbs, RA
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 245 (1-2) : 8 - 11
  • [32] 2-(CHLOROMETHYL)-2-(TRIMETHYLSILYL)-1-PROPENE - A CONVENIENT REAGENT FOR THE SYNTHESIS OF METHYLENETETRAHYDROFURANS AND METHYLENEBUTYROLACTONES
    DANIELLO, F
    MATTII, D
    TADDEI, M
    SYNLETT, 1993, (02) : 119 - 121
  • [33] NEW SYNTHESIS OF O-NITROBENZYLKETONES - INTERMEDIATES FOR SYNTHESIS OF 2-SUBSTITUTED INDOLES
    GARCIA, EE
    FRYER, RI
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (02) : 219 - 221
  • [34] CONVENIENT SYNTHESIS OF BENZO[B]TROPONES FUSED WITH INDOLIZINES OR INDOLES BY REACTION OF 2-PHENYL-3-VINYL SUBSTITUTED DERIVATIVES WITH POLYPHOSPHORIC ACID
    YAMASHITA, Y
    SUZUKI, D
    MASUMURA, M
    HETEROCYCLES, 1984, 22 (04) : 791 - 794
  • [35] FACILE SYNTHESIS OF 2-SUBSTITUTED INDOLES FROM ORTHO-BROMOANILINE
    SAKAMOTO, T
    KONDO, Y
    YAMANAKA, H
    HETEROCYCLES, 1986, 24 (01) : 31 - 32
  • [36] THE REACTION OF VINYL GRIGNARD-REAGENTS WITH 2-SUBSTITUTED NITROARENES - A NEW APPROACH TO THE SYNTHESIS OF 7-SUBSTITUTED INDOLES
    BARTOLI, G
    PALMIERI, G
    BOSCO, M
    DALPOZZO, R
    TETRAHEDRON LETTERS, 1989, 30 (16) : 2129 - 2132
  • [37] General approach to 2-substituted indoles.
    Smitrovich, JH
    Qu, CX
    Davies, IW
    Hughes, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U110 - U110
  • [38] A NEW PROCEDURE FOR THE SYNTHESIS OF 2-SUBSTITUTED INDOLES AND 2,2'-BI-INDOLYLS
    SAITO, I
    MORII, T
    MATSUGO, S
    MATSUURA, T
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (17) : 977 - 979
  • [39] Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol
    Zhao, Guangkuan
    Roudaut, Christelle
    Gandon, Vincent
    Alami, Mouad
    Provot, Olivier
    GREEN CHEMISTRY, 2019, 21 (15) : 4204 - 4210
  • [40] A facile synthesis of 2-substituted indoles from (2-aminobenzyl)triphenylphosphonium salts
    Taira, S
    Danjo, H
    Imamoto, T
    TETRAHEDRON LETTERS, 2002, 43 (16) : 2885 - 2888
12345