Selective Base Promoted Synthesis of Dihydroisobenzofurans by Domino Addition/ Annulation Reactions of ortho-Alkynylbenzaldehydes
Articolo
Data di Pubblicazione:
2010
Citazione:
Selective Base Promoted Synthesis of Dihydroisobenzofurans by Domino Addition/
Annulation Reactions of ortho-Alkynylbenzaldehydes / M. Dell'Acqua, D. Facoetti, G. Abbiati, E. Rossi. - In: SYNTHESIS. - ISSN 0039-7881. - 2010:14(2010), pp. Z06110SS.2367-Z06110SS.2378. [10.1055/s-0029-1218766]
Abstract:
The synthesis of dihydroisobenzofuran nucleus was achieved by the base promoted tandem nucleophilic addition/
annulation reaction of ortho-alkynylbenzaldehydes in the presence of methanol. The reactions of aryl-, trimethylsilyl- and
diethoxymethyl-substituted alkynylbenzaldehydes occurred with
complete regioselectivity in good to excellent yields under microwaves
irradiation. The reactions of alkyl substituted alkynylbenzaldehydes
took place with good yields and high regioselectivity
only when performed at room temperature and in the presence of a
catalytic amount of a gold(III) salt. The plausible reaction mechanisms
involved were discussed. The effect of the substituent at the
alkynyl terminus on the cyclization mode was tentatively rationalized.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
alkynes ; heterocycles ; domino reaction ; microwave-promoted synthesis ; gold
Elenco autori:
M. Dell'Acqua, D. Facoetti, G. Abbiati, E. Rossi
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