Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins

Manoj R. Zanwar, Mustafa J. Raihan, Sachin D. Gawande, Veerababurao Kavala, Donala Janreddy, Chun Wei Kuo, Ram Ambre, Ching-Fa Yao

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20 Citations (Scopus)

Abstract

The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3- carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated.

Original languageEnglish
Pages (from-to)6495-6504
Number of pages10
JournalJournal of Organic Chemistry
Volume77
Issue number15
DOIs
Publication statusPublished - 2012 Aug 3

ASJC Scopus subject areas

  • Organic Chemistry

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    Zanwar, M. R., Raihan, M. J., Gawande, S. D., Kavala, V., Janreddy, D., Kuo, C. W., Ambre, R., & Yao, C-F. (2012). Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins. Journal of Organic Chemistry, 77(15), 6495-6504. https://doi.org/10.1021/jo301044y