Alcohol Mediated Synthesis of 4‑Oxo-2-aryl‑4H‑chromene-3-carboxylate Derivatives from 4‑Hydroxycoumarins

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 m...

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Veröffentlicht in:	Journal of organic chemistry 2012-08, Vol.77 (15), p.6495-6504
Hauptverfasser:	Zanwar, Manoj R, Raihan, Mustafa J, Gawande, Sachin D, Kavala, Veerababurao, Janreddy, Donala, Kuo, Chun-Wei, Ambre, Ram, Yao, Ching-Fa
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Hydroxycoumarins - chemistry Alcohols - chemistry Benzopyrans - chemical synthesis Benzopyrans - chemistry Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Models, Molecular Molecular Structure Organic chemistry Preparations and properties
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Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo301044y