1246365-03-6Relevant articles and documents
Selective base-promoted synthesis of dihydroisobenzofurans by domino addition/annulation reactions of ortho-alkynylbenzaldehydes
Dell'Acqua, Monica,Facoetti, Diego,Abbiati, Giorgio,Rossi, Elisabetta
, p. 2367 - 2378 (2010)
Synthesis of the 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 microwave 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. Plausible reaction mechanisms involved are discussed. The effect of the substituent at the alkynyl terminus on the cyclisation mode was tentatively rationalised. Georg Thieme Verlag Stuttgart · New York.