Modern organic chemistry demands green and sustainable methods for the synthesis of simple and complex functional molecules. In this regard, construction of various heterocyclic rings has gained much importance in the field of organic and medicinal chemistry. Pyrrole is a privileged framework which comprises of scaffolds present in many drugs, natural products and biologically active compounds. Research work in our group is mainly focussed on the development of new methods for the molecular-diversity feasible synthesis of novel heterocycles, utilization of developed methods in preparation of rationally designed target-specific inhibitors and bioevaluation studies. The present study depicts a novel and efficient one step strategy for the synthesis of polysubstituted pyrroles. The reaction involved generation of <i>vic</i>-dinitrile followed by cyanide-mediated nitrile-to-nitrile intramolecular cyclocondensation in a tertiary amine base promoted reaction of <i>gem</i>-diactivated acrylonitrile with TMSCN. The present work represents for the first time a cyanide mediated nitrile-to-nitrile intramolecular cyclization, adding a new method into the list of conventional ring closure reactions. Utilizing the developed method, versatile polysubstituted pyrroles have been synthesized, which possess multiple C/N-nucleophilic as well as electrophilic reactive centres. This presentation will highlight the development of method, utilization in the preparation of compounds with relevant biological substitutions/functionalities, detailed investigation for identifying the plausible mechanism and its further extension for the synthesis of fused heterocycles.

Cyanide-mediated nitrile-to-nitrile cyclocondensation towards efficient synthesis of polysubstituted pyrroles

2019 Spring National Meeting

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