Novel indole-ring formation by thermolysis of 2-(N-acylamino)-benzylphosphonium salts. Effective synthesis of 2-trifluoromethyl-indoles

被引：36

作者：

Miyashita, K ^{[1
]}

Kondoh, K ^{[1
]}

Tsuchiya, K ^{[1
]}

Miyabe, H ^{[1
]}

Imanishi, T ^{[1
]}

机构：

[1] OSAKA UNIV,FAC PHARMACEUT SCI,SUITA,OSAKA 565,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 11期

关键词：

D O I：

10.1039/p19960001261

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermolysis of 2-(N-acylamino)benzyl methyl ethers, in the presence of an acid catalyst and triphenylphosphine, or 2-(N-acylamino)benzylphosphonium salts is found to serve as a novel method for indole formation, in particular for the Synthesis of 2-trifluoromethylindoles. The reaction of the benzyl methyl ethers is suggested to involve a phosphonium intermediate, which thermally decomposes to the indoles.

引用

页码：1261 / 1268

页数：8

共 40 条

[1] FLASH VACUUM PYROLYSIS OF STABILIZED PHOSPHORUS YLIDES .1. PREPARATION OF ALIPHATIC AND TERMINAL ALKYNES
AITKEN, RA
ATHERTON, JI
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (10): : 1281 - 1284
[2] [Anonymous], 1994, CONTEMP ORG SYNTH
[3] 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
[J]. TETRAHEDRON, 1990, 46 (04) : 1379 - 1384
[4] INTRAMOLECULAR PETERSON OLEFINATION OF ORTHO-TRIMETHYLSILYLMETHYL ANILIDES - A NEW SYNTHESIS OF N-METHYLINDOLES
BARTOLI, G
BOSCO, M
DALPOZZO, R
TODESCO, PE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) : 807 - 808
[5] BIRUM GH, 1967, J CHEM SOC CHEM COMM, P137
[6] FLUORINATED ORGANOMETALLICS - PERFLUOROALKYL AND FUNCTIONALIZED PERFLUOROALKYL ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS
BURTON, DJ
YANG, ZY
[J]. TETRAHEDRON, 1992, 48 (02) : 189 - 275
[7] NEW SYNTHESES OF 2-ACYLBENZOFURANS, 2-ACYLINDOLES, 2-INDOLYLCARBOXYLATES, AND 2-QUINOLONES BY INTRAMOLECULAR WITTIG REACTION
CAPUANO, L
AHLHELM, A
HARTMANN, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (06): : 2069 - 2074
[8] PHOTOINDUCED ELECTRON-TRANSFER REACTION OF DIFLUORODIIODOMETHANE WITH AZA-AROMATIC COMPOUNDS AND ENAMINES
CHEN, QY
LI, ZT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (06): : 645 - 648
[9] CREASEY WA, 1983, INDOLES 4, P783
[10] FILLER R, 1986, FLUORINE 1ST 100 YEA, P361

← 1 2 3 4 →