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^*

^*Corresponding author for this work

Department of Chemistry

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

30 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

Access to Document

10.1021/jo301044y

Cite this

@article{b4c27fcfbf8648399b8616d7ede6c6d8,

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 Yao, {Ching Fa}",

year = "2012",

month = aug,

day = "3",

doi = "10.1021/jo301044y",

language = "English",

volume = "77",

pages = "6495--6504",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins

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.

UR - http://www.scopus.com/inward/record.url?scp=84864620344&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84864620344&partnerID=8YFLogxK

U2 - 10.1021/jo301044y

DO - 10.1021/jo301044y

M3 - Article

C2 - 22809001

AN - SCOPUS:84864620344

SN - 0022-3263

VL - 77

SP - 6495

EP - 6504

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 844724: Experimental Crystal Structure Determination

Cite this

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 844724: Experimental Crystal Structure Determination

Cite this