Chlorination of 2-substituted 1-hydroxyindoles

被引：2

作者：

Chirkova, Zh. V. ^{[1
]}

Kabanova, M. V. ^{[1
]}

Filimonov, S. I. ^{[1
]}

Samet, A. V. ^{[2
]}

Stashina, G. A. ^{[2
]}

Sudzilovskaya, T. N. ^{[1
]}

机构：

[1] Yaroslavl State Tech Univ, 88 Moskovskii Prosp, Yaroslavl 150023, Russia

[2] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2018年 / 67卷 / 06期

关键词：

chlorination; N-chlorosuccinimide; 1-hydroxyindole-5,6-dicarbonitriles; 1-hydroxypyrrolo[3,4-f]indole-5,7(1H,6H)-diones; 3,3-dichloro-3H-indole 1-oxides; 3-chloro-1-hydroxyindole-5,6-dicarbonitriles; 3-chloroindole-5,6-dicarbonitriles; reduction; TERTIARY AMINE OXIDES; EFFICIENT SYNTHESIS; MONOAMINE-OXIDASE; IN-SITU; DERIVATIVES; HALOGENATION; ACID; OXIDATION; ESTER;

D O I：

10.1007/s11172-018-2184-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chlorination of 1-hydroxyindole-5,6-dicarbonitriles and 1-hydroxypyrrolo[3,4-f]indole-5,7(1H,6H)-diones with N-chlorosuccinimide afforded previously unknown 3,3-dichloro-3Hindole 1-oxides instead of the expected 3-chloro-1-hydroxyindoles. The latter, however, were prepared in good yields by treatment of the above 3,3-dichloro-3H-indole 1-oxides with piperidine in ethanol. Reduction of 3,3-dichloro-5,6-dicyano-3H-indole 1-oxides with Zn in AcOH yielded the corresponding 3-chloroindole-5,6-dicarbonitriles.

引用

页码：1083 / 1087

页数：5

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