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.

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页码：1261 / 1268

页数：8

相关论文

共 40 条

[1] FLASH VACUUM PYROLYSIS OF STABILIZED PHOSPHORUS YLIDES .1. PREPARATION OF ALIPHATIC AND TERMINAL ALKYNES [J].

AITKEN, RA ;

ATHERTON, JI .

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 [J].

BARTOLI, G ;

PALMIERI, G ;

PETRINI, M ;

BOSCO, M ;

DALPOZZO, R .

TETRAHEDRON, 1990, 46 (04) :1379-1384

[4] INTRAMOLECULAR PETERSON OLEFINATION OF ORTHO-TRIMETHYLSILYLMETHYL ANILIDES - A NEW SYNTHESIS OF N-METHYLINDOLES [J].

BARTOLI, G ;

BOSCO, M ;

DALPOZZO, R ;

TODESCO, PE .

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 [J].

BURTON, DJ ;

YANG, ZY .

TETRAHEDRON, 1992, 48 (02) :189-275

[7] NEW SYNTHESES OF 2-ACYLBENZOFURANS, 2-ACYLINDOLES, 2-INDOLYLCARBOXYLATES, AND 2-QUINOLONES BY INTRAMOLECULAR WITTIG REACTION [J].

CAPUANO, L ;

AHLHELM, A ;

HARTMANN, H .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (06) :2069-2074

[8] PHOTOINDUCED ELECTRON-TRANSFER REACTION OF DIFLUORODIIODOMETHANE WITH AZA-AROMATIC COMPOUNDS AND ENAMINES [J].

CHEN, QY ;

LI, ZT .

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

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