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

doi:10.1021/jo301044y

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	6495-6504
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	77
Issue number	15
DOIs	https://doi.org/10.1021/jo301044y
Publication status	Published - 2012 Aug 3

ASJC Scopus subject areas

Organic Chemistry

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Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins. / Zanwar, Manoj R.; Raihan, Mustafa J.; Gawande, Sachin D.; Kavala, Veerababurao; Janreddy, Donala; Kuo, Chun Wei; Ambre, Ram; Yao, Ching-Fa.

In: Journal of Organic Chemistry, Vol. 77, No. 15, 03.08.2012, p. 6495-6504.

Research output: Contribution to journal › Article › peer-review

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

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.",

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

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AU - Zanwar, Manoj R.

AU - Raihan, Mustafa J.

AU - Gawande, Sachin D.

AU - Kavala, Veerababurao

AU - Janreddy, Donala

AU - Kuo, Chun Wei

AU - Ambre, Ram

AU - Yao, Ching-Fa

PY - 2012/8/3

Y1 - 2012/8/3

N2 - 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.

AB - 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.

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

Abstract

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