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.
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.
|Titolo:||Selective Base Promoted Synthesis of Dihydroisobenzofurans by Domino Addition/ Annulation Reactions of ortho-Alkynylbenzaldehydes|
DELL'ACQUA, MONICA (Primo)
FACOETTI, DIEGO (Secondo)
ABBIATI, GIORGIO (Corresponding)
ROSSI, ELISABETTA (Ultimo)
|Parole Chiave:||alkynes ; heterocycles ; domino reaction ; microwave-promoted synthesis ; gold|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2010|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1055/s-0029-1218766|
|Appare nelle tipologie:||01 - Articolo su periodico|