Efficient selective synthesis of 2-substituted indoles from complex-base-promoted arynic cyclisations

被引：9
作者：
KuehmCaubere, C
Rodriguez, I
Pfeiffer, B
Renard, P
Caubere, P
机构：
[1] UNIV NANCY 1,FAC SCI,LAB CHIM ORGAN 1,CNRS,URA 457,F-54506 VANDOEUVRE NANCY,FRANCE
[2] ADIR,F-92415 COURBEVOIE,FRANCE
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 19期
关键词：
D O I：
10.1039/a702548c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Substituted indoles have been efficiently obtained by selective arynic cyclisation of halogenated aryl imines of methyl ketones in the presence of the complex-base NaNH2-(BuONa)-O-t and by PhCH2SH-AlCl3 opening of tetrahydrothiopyranoindoles also obtained from arynic cyclisation of imines.
引用
收藏
页码：2857 / 2862
页数：6
相关论文
共 36 条
[1]  
[Anonymous], 1994, CONTEMP ORG SYNTH
[2]   AN ANTIMALARIAL ALKALOID FROM HYDRANGEA .6. A 2ND SYNTHESIS OF 3-[BETA-KETO-GAMMA-(2-PIPERIDYL)-PROPYL]-4-QUINAZOLONE [J].
BAKER, BR ;
QUERRY, MV ;
SCHAUB, RE ;
WILLIAMS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1952, 17 (01) :58-67
[3]  
BOUISSET M, 1980, Patent No. 7930039
[4]  
BOUISSETT M, 1979, Patent No. 7930039
[5]   Intramolecular radical substitution reactions: A novel approach to fused [1,2-a]indoles [J].
Caddick, S ;
Aboutayab, K ;
Jenkins, K ;
West, RI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (07) :675-682
[6]   AGGREGATIVE ACTIVATION AND HETEROCYCLIC CHEMISTRY .1. COMPLEX BASES PROMOTED ARYNIC CYCLIZATION OF IMINES OR ENAMINOKETONES - REGIOCHEMICAL SYNTHESIS OF INDOLES [J].
CAUBERE, C ;
CAUBERE, P ;
IANELLI, S ;
NARDELLI, M ;
JAMARTGREGOIRE, B .
TETRAHEDRON, 1994, 50 (41) :11903-11920
[7]   FUNCTIONALIZATION OF THE ALKOXY GROUP OF ALKYL ARYL ETHERS - DEMETHYLATION, ALKYLTHIOLATION AND REDUCTION OF 5-METHOXYINDOLES [J].
CAUBERE, C ;
CAUBERE, P ;
RENARD, P ;
BIZOTESPIART, JG ;
IANELLI, S ;
NARDELLI, M ;
JAMARTGREGOIRE, B .
TETRAHEDRON, 1994, 50 (47) :13433-13448
[8]   UNIMETAL SUPER BASES [J].
CAUBERE, P .
CHEMICAL REVIEWS, 1993, 93 (06) :2317-2334
[9]  
CAUBERE P, 1991, REV HETEROATOM CHEM, V4, P78
[10]   IS N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE A GOOD LIGAND FOR LITHIUM [J].
COLLUM, DB .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (10) :448-454
1234