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
  • [21] THE CHEMISTRY OF INDOLES .45. A CONVENIENT SYNTHETIC METHOD OF 2-SUBSTITUTED INDOLES AND ITS APPLICATION FOR THE SYNTHESIS OF NATURAL ALKALOID, BORRERINE
    SOMEI, M
    SAYAMA, S
    NAKA, K
    YAMADA, F
    HETEROCYCLES, 1988, 27 (07) : 1585 - 1587
  • [22] A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
    Irgashev, Roman A.
    Karmatsky, Arseny A.
    Rusinov, Gennady L.
    Charushin, Valery N.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1000 - 1007
  • [23] Synthesis of new substituted 2-(trimethylstannyl)indoles
    Kumar, Arvind
    Say, Martial
    Boykin, David W.
    SYNTHESIS-STUTTGART, 2008, (05): : 707 - 710
  • [24] A convenient synthesis of 2-cyano-3-substituted indoles
    Denison, S
    Hilton, ST
    SYNLETT, 2004, (15) : 2806 - 2808
  • [25] A FACILE ROUTE TO 2-SUBSTITUTED INDOLES
    MADSEN, JO
    MELDAL, M
    MORTENSEN, S
    OLSSON, B
    ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1981, 35 (02): : 77 - 81
  • [26] A NEW APPROACH TO THE SYNTHESIS OF 2-SUBSTITUTED INDOLES - REACTION OF DIMETALLATED ORTHO-TRIMETHYLSILYLMETHYLANILIDES WITH ESTERS
    BARTOLI, G
    PALMIERI, G
    PETRINI, M
    BOSCO, M
    DALPOZZO, R
    TETRAHEDRON, 1990, 46 (04) : 1379 - 1384
  • [27] Synthesis of 2-substituted indoles via a palladium-catalyzed domino Heck reaction and dealkylation
    Mao, Hui
    Wan, Jie-Ping
    Pan, Yuanjiang
    Sun, Cuirong
    TETRAHEDRON LETTERS, 2010, 51 (14) : 1844 - 1846
  • [28] ZnCl2 and Pd/C catalyzed synthesis of 2-substituted indoles
    Ahmed, Atiur
    Ghosh, Munmun
    Sarkar, Pompy
    Ray, Jayanta K.
    TETRAHEDRON LETTERS, 2013, 54 (49) : 6691 - 6694
  • [29] A convenient synthesis of 2-substituted thiazole-5-carboxylates
    Fong, M
    Janowski, WK
    Prager, RH
    Taylor, MR
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (06) : 599 - 604
  • [30] CONVENIENT PREPARATION OF 2-SUBSTITUTED BENZOTHIAZOLES
    BOGER, DL
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11): : 2296 - 2297
12345