3H-INDOLES .2. SYNTHESIS OF 3-ALKYL-3H-INDOLES BY ALKYLATION OF 2,3-DISUBSTITUTED INDOLES WITH POLYPHOSPHATE ESTER AND SOME REACTIONS OF 3H-INDOLE SYSTEM

被引：20

作者：

KANAOKA, Y

MIYASHIT.K

YONEMITS.O

机构：

[1] Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo

来源：

TETRAHEDRON | 1969年 / 25卷 / 14期

关键词：

D O I：

10.1016/0040-4020(69)80019-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reaction mixture of alcohol and phosphorus pentoxide, forming a new type of polyphospbate ester (PPE), is proposed as an alkylating agent of 2,3-disubstituted indoles for the synthesis of 3-alkyl-3H-indoles. Thus 1,2,3,4-tetrahydrocarbazole 1 and 2,3-dimethylindole 10 are methylated or ethylated to afford corresponding 3H-indoles in approx. 40-70% yield. The Plancher rearrangement of substituted 3H-indoles is realized including an interesting carbazolenine ∼ indolenine ring isomerism". Facile autoxidation of the methylene carbon at the 2-position of 3H-indole is observed and discussed. © 1969."

引用

页码：2757 / &

共 42 条

[1] PEROXIDES OF TETRAHYDROCARBAZOLE AND RELATED COMPOUNDS .2. [J].