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.
BEER, RJS
MCGRATH, L
ROBERTSON, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (NOV): : 3283 - 3286
[2] PEROXIDES OF TETRAHYDROCARBAZOLE AND RELATED COMPOUNDS .1. TETRAHYDROCARBAZOLYL HYDROPEROXIDE
BEER, RJS
MCGRATH, L
ROBERTSON, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (AUG): : 2118 - 2126
[3] PEROXIDES OF TETRAHYDROCARBAZOLE AND RELATED COMPOUNDS .4. AUTOXIDATION OF SUBSTITUTED TETRAHYDROCARBAZOLES
BEER, RJS
BROADHURST, T
ROBERTSON, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC): : 4946 - 4951
[4] PEROXIDES OF TETRAHYDROCARBAZOLE AND RELATED COMPOUNDS .5. 8-BROMO-1-2-3-4-TETRAHYDROCARBAZOLE
BEER, RJS
BROADHURST, T
ROBERTSON, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (AUG): : 2440 - 2442
[5] BHACCA MS, 1962, NMR SPECTRA CATAL ED
[6] ELDERFIELD RC, 1952, HETEROCYCLIC COMP ED, V3, P102
[7] MOLECULAR REARRANGEMENTS .8. EQUILIBRATION OF 3,3-DIMETHYL-2-PHENYL- AND 2,3-DIMETHYL-3-PHENYL-3H-INDOLES
EVANS, FJ
WATKINS, J
LYLE, RE
LYLE, GG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) : 1553 - &
[8] 2-ETHOXYINDOLES AND 2-ETHYLTHIOINDOLES - THEIR AUTOXIDATION AND REACTIONS WITH PIPERIDINE
HINO, T
NAKAGAWA, M
AKABOSHI, S
[J]. CHEMICAL COMMUNICATIONS, 1967, (13) : 656 - &
[9] ISOE S, 1959, CHEM IND-LONDON, P1574
[10] ELECTROPHILIC SUBSTITUTION IN INDOLES .3. REARRANGEMENT OF 3,3-DIALKYL INDOLENINES
JACKSON, AH
SMITH, P
[J]. TETRAHEDRON, 1968, 24 (05) : 2227 - &

← 1 2 3 4 5 →