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 | |
| Publication status | Published - 2012 Aug 3 |
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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 journal › Article
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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 -