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


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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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