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Issue 14, 2018
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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

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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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Publication details

The article was received on 30 Jan 2018, accepted on 27 May 2018 and first published on 28 May 2018


Article type: Letter
DOI: 10.1039/C8NJ00490K
Citation: New J. Chem., 2018,42, 11280-11284
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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

    M. A. Waseem, R. A. Rather, M. Saquib, A. Ibad, F. Ibad, K. Ansari, M. A. Khuroo, M. A. Assiri and I. R. Siddiqui, New J. Chem., 2018, 42, 11280
    DOI: 10.1039/C8NJ00490K

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