Chlorination of 2-substituted 1-hydroxyindoles
- Authors: Chirkova Z.V.1, Kabanova M.V.1, Filimonov S.I.1, Samet A.V.2, Stashina G.A.2, Sudzilovskaya T.N.1
-
Affiliations:
- Yaroslavl State Technical University
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Issue: Vol 67, No 6 (2018)
- Pages: 1083-1087
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/242635
- DOI: https://doi.org/10.1007/s11172-018-2184-6
- ID: 242635
Cite item
Abstract
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.
About the authors
Zh. V. Chirkova
Yaroslavl State Technical University
Author for correspondence.
Email: chirkovazhv@ystu.ru
Russian Federation, 88 Moskovskii prosp., Yaroslavl, 150023
M. V. Kabanova
Yaroslavl State Technical University
Email: chirkovazhv@ystu.ru
Russian Federation, 88 Moskovskii prosp., Yaroslavl, 150023
S. I. Filimonov
Yaroslavl State Technical University
Email: chirkovazhv@ystu.ru
Russian Federation, 88 Moskovskii prosp., Yaroslavl, 150023
A. V. Samet
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: chirkovazhv@ystu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
G. A. Stashina
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: chirkovazhv@ystu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
T. N. Sudzilovskaya
Yaroslavl State Technical University
Email: chirkovazhv@ystu.ru
Russian Federation, 88 Moskovskii prosp., Yaroslavl, 150023