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 mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated.
Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, Taiwan 116, R.O.C.
Manoj R
MR
Zanwar
Mustafa J
MJ
Raihan
Sachin D
SD
Gawande
Veerababurao
V
Kavala
Donala
D
Janreddy
Chun-Wei
CW
Kuo
Ram
R
Ambre
Ching-Fa
CF
Yao
D015110:4-Hydroxycoumarins / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure
D015110:4-Hydroxycoumarins; D000438:Alcohols; D001578:Benzopyrans; C068805:4-hydroxycoumarin