Chemoselective Condensation of β-Naphthol, Dimethyl Malonate, and Aromatic Aldehydes Promoted by Niobium Pentachloride

A multicomponent reaction of β -naphthol, dimethyl malonate, and aromatic aldehydes in the presence of NbCl 5 as promoter is described. Under similar conditions, aromatic aldehydes with different substituents exhibited different behaviors than β -naphthol and dimethyl malonate. In these MCRs, 4-aryl...

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Bibliographic Details
Published in:Synthetic communications 2015-05, Vol.45 (9), p.1114-1126
Main Authors: Bartolomeu, Aloisio de Andrade, de Menezes, Manoel Lima, Silva-Filho, Luiz Carlos da
Format: Article
Language:English
Subjects:
4-Aryl-3,4-dihydrobenzo[f]coumarins
chemoselective
Lewis acid
multicomponent reactions
niobium pentachloride
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Summary:A multicomponent reaction of β -naphthol, dimethyl malonate, and aromatic aldehydes in the presence of NbCl 5 as promoter is described. Under similar conditions, aromatic aldehydes with different substituents exhibited different behaviors than β -naphthol and dimethyl malonate. In these MCRs, 4-aryl-3,4-dihydrobenzo[f]coumarins are obtained as the major products (41-93%) and 14-aryl-14H-dibenzo[a,j]xanthenes as the minor products (1-38%).
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2014.999341