Heterocyclization of o-(arylethynyl)arylhydrazines as a new procedure for the synthesis of substituted 1H- and 2H-indazoles and indoles

被引：10
作者：
Prikhodko, TA [1 ]
Vasilevsky, SF [1 ]
机构：
[1] Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2001年 / 50卷 / 07期
关键词：
indazoles; isoindazoles; indoles; cross-coupling; o-iodoarylhydrazines; o-chloroarylacetylenes; heterocyclization;
D O I：
10.1023/A:1014071226473
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Procedures for the preparation of 3-substituted 1H- and 2H-indazoles and 2-substituted indoles were developed based on cross-coupling of o-iodoarylhydrazines with copper acetylenides in pyridine or dimethylforamide. An alternative procedure for the synthesis of 3-substituted 1H-indazoles involves cyclocondensation of (2-chloroaryl)acetylenes with hydrazine hydrate in butanol.
引用
收藏
页码：1268 / 1273
页数：6
相关论文
共 17 条
  • [1] SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYZED BY PALLADIUM COMPOUNDS
    AMES, DE
    BULL, D
    [J]. TETRAHEDRON, 1982, 38 (03) : 383 - 387
  • [2] EQUILIBRIUM CH ACIDITY OF ACETYLENIC DERIVATIVES OF N-ALKYLAZOLES IN DMSO
    BELOV, AI
    TEREKHOVA, MI
    PETROV, ES
    VASILEVSKII, SF
    SHVARTSBERG, MS
    [J]. BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (03): : 398 - 402
  • [3] BRANDSMA L, 1998, APPL TRANSITION META, P220
  • [4] BUMAGIN NA, 1984, SYNTHESIS-STUTTGART, P728
  • [5] THE PREPARATION OF SUBSTITUTED HYDRAZINES .4. ARYLHYDRAZINES VIA CONVENTIONAL METHODS
    HUNSBERGER, IM
    SHAW, ER
    FUGGER, J
    KETCHAM, R
    LEDNICER, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) : 394 - 399
  • [6] KOST AN, 1960, DOKL AKAD NAUK SSSR+, V130, P326
  • [7] Prikhod'ko TA, 1998, MENDELEEV COMMUN, P149
  • [8] ACETYLENIC-COMPOUNDS AS INTERMEDIATES IN HETEROCYCLIC SYNTHESIS - REACTION OF 1-ACETYLENYLANTHRAQUINONES WITH HYDRAZINE
    SHVARTSBERG, MS
    IVANCHIKOVA, ID
    VASILEVSKY, SF
    [J]. TETRAHEDRON LETTERS, 1994, 35 (13) : 2077 - 2080
  • [9] STEPHENS RD, 1963, J ORG CHEM, V28, P3313, DOI 10.1021/jo01047a008
  • [10] EQUILIBRIUM CH ACIDITY OF ARYLACETYLENES IN DIMETHYLSULFOXIDE
    TEREKHOVA, MI
    PETROV, ES
    VASILEVSKII, SF
    IVANOV, VF
    SHVARTSBERG, MS
    [J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1984, 33 (04): : 850 - 852
12