Synthesis of substituted disulfonyl-containing polycyclic azines with the bridgehead nitrogen atom. Effects of the structure of 3-substituted pyridinium ylides on the regioselectivity of their reactions with E-1,2-di(alkylsulfonyl)-1,2-dichloroethenes
- Authors: Dontsova N.E.1, Shestopalov A.M.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Issue: Vol 66, No 6 (2017)
- Pages: 1030-1043
- Section: Full Articles
- URL: https://journal-vniispk.ru/1066-5285/article/view/240739
- DOI: https://doi.org/10.1007/s11172-017-1851-3
- ID: 240739
Cite item
Abstract
Heating the substituted pyridinium and isoquinolinium salts with E-1,2-di(alkylsulfonyl)-1,2-dichloroethenes in either chloroform or acetone in the presence of three-fold excess of Et3N gave high yields of substituted 1,2-di(alkylsulfonyl)indolizines and 1,2-di(alkylsulfonyl) pyrrolo[2,1-a]isoquinolines, respectively. Effects of the structure of 3-substituted pyridinium ylides on the regioselectivity of their reaction with E-1,2-di(alkylsulfonyl)-1,2-dichloroethenes were revealed. It was shown that the presence of electron-releasing and electron-withdrawing substituents in the pyridinium ylide favors the formation of 8-substituted and 6-substituted 1,2-(dialkylsulfonyl)indolizines, respectively.
About the authors
N. E. Dontsova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: gsv@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. M. Shestopalov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: gsv@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
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