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[bmIm]Br catalyzed tandem construction of C–C and C–O bonds: a concise, convenient and atom-economical strategy for the synthesis of spiropyranopiperidine derivatives†
Malik A. Waseem,Rafiq A. Rather,Mohammad Saquib,Afshan Ibad,Farah Ibad,Khursheed Ansari,M. A. Khuroo,Mohammed A. Assiri,I. R. Siddiqui
New Journal of Chemistry Pub Date : 05/28/2018 00:00:00 , DOI:10.1039/C8NJ00490K
Abstract

A versatile one-pot domino access to chiral heterocyclic spiropyranopiperidine has been reported. This novel approach involves recyclable [bmIm]Br as a promoter as well as a reaction medium and KOH as a non-hazardous base for the facile chemical unification of DMAD, malononitrile and 1-methyl-4-piperidone, resulting in the formation of spiropyranopiperidine in an excellent yield after 3 hours under mild reaction conditions. This green and efficient methodology leads to a significant enhancement of the yield of product, elimination of the use of toxic and hazardous reagents and reduced waste formation. A plausible mechanism for the multiple bond forming heterocyclisation has also been proposed.

Graphical abstract: [bmIm]Br catalyzed tandem construction of C–C and C–O bonds: a concise, convenient and atom-economical strategy for the synthesis of spiropyranopiperidine derivatives
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