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Issue 26, 2014
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An efficient catalyst free synthesis of nitrogen containing spiro heterocycles via [5 + 1] double Michael addition reaction

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Abstract

2,4-Diazaspiro[5.5]undecane-1,3,5,9-tetraones and 3-thioxo-2,4-diazaspiro[5.5]undecane-1,5,9-triones have been synthesized via double Michael addition of 1,5-diaryl-1,4-pentadien-3-one with active methylene compounds such as N,N-dimethyl barbituric acid, barbituric acid, thio-barbituric acid and N,N-diphenyl thiobarbituric acid in ethylene glycol at 100 °C in the absence of any catalyst to give high yields within a short reaction time. The structure has been confirmed by X-ray analysis. The single-crystal structure of the diazaspiro compound revealed that the CAr–H⋯π, π–π stacking and intermolecular hydrogen bonding interactions act as major driving forces for crystal packing.

Graphical abstract: An efficient catalyst free synthesis of nitrogen containing spiro heterocycles via [5 + 1] double Michael addition reaction

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Publication details

The article was received on 18 Jan 2014, accepted on 24 Feb 2014 and first published on 26 Feb 2014


Article type: Paper
DOI: 10.1039/C4RA00521J
RSC Adv., 2014,4, 13313-13321

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    An efficient catalyst free synthesis of nitrogen containing spiro heterocycles via [5 + 1] double Michael addition reaction

    K. Aggarwal, K. Vij and J. M. Khurana, RSC Adv., 2014, 4, 13313
    DOI: 10.1039/C4RA00521J

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