Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines.

Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and catalysts and can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates.

Microwave-accelerated and efficient synthesis of structurally diverse N-(2,2-diphenylvinyl)-ß-oxoamides.

N-(2,2-Diphenylvinyl)-ß-oxoamides are both the structural moiety of biologically active compounds and important synthetic intermediates. Structurally diverse N-(2,2-diphenylvinyl)-ß-oxoamides are prepared efficiently from 2-diazo-1,3-dicarbonyl compounds and N-alkyl-2,2-diphenylaziridines via an electrophilic ring opening reaction under two different reaction conditions of reflux and microwave irradiation. 2-Diazo-1,3-dicarbonyl compounds undergo the Wolff rearrangement under heating to generate α-oxoketenes, which electrophilically react with N-alkylaziridines to directly produce structurally diverse N-(2,2-diphenylvinyl)-ß-oxoamides in good to excellent yields under microwave irradiation. Microwave irradiation accelerates the reaction obviously and efficiently. Both 2-diazo-1,3-diketones and alkyl 2-diazo-3-oxoalkanoates work well. The reaction is catalyst-free and highly atom economical, involves only loss of nitrogen and does not require additives. The products are useful synthons for the convenient preparation of multisubstituted ß-lactam derivatives.