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

Research output: Contribution to journalArticle

18 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

Fingerprint

4-Hydroxycoumarins
Benzopyrans
flavone
Alcohols
Derivatives
Ions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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 journalArticle

Zanwar, MR, Raihan, MJ, Gawande, SD, Kavala, V, Janreddy, D, Kuo, CW, 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, vol. 77, no. 15, pp. 6495-6504. https://doi.org/10.1021/jo301044y
Zanwar, Manoj R. ; Raihan, Mustafa J. ; Gawande, Sachin D. ; Kavala, Veerababurao ; Janreddy, Donala ; Kuo, Chun Wei ; Ambre, Ram ; Yao, Ching-Fa. / Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 15. pp. 6495-6504.
@article{39005d71b10040248ae4938fd5bb038c,
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",
year = "2012",
month = "8",
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

VL - 77

SP - 6495

EP - 6504

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -