Synthetic application of azetidin-2-ones to a synthesis of furan derivatives

Abstract

2-(1-Anilinoethyl)but-2-enolides (8a and b) were synthesized from 4-methyl-1-phenylazetidin-2-one and the appropriate ketones. In the same way, 2-(1-anilinobutyl)but-2-enolides (12a and b) were obtained by the use of 1-phenyl-4-propylazetidin-2-one. These butenolides were converted into the corresponding furan derivatives by reduction with di-isobutylaluminium hydride. Phenylation of the butenolides with phenyl-lithium or phenylmagnesium bromide yielded the corresponding 2-phenylfuran derivatives. Furthermore, 3-anilinomethyl-2-methyland -ethyl-4,5,6,7-tetrahydrobenzo[b]furan were obtained from the butenolide (15) with methyl- or ethylmagnesium iodide, respectively.