Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate

Beilstein J Org Chem. 2013 Dec 27:9:2934-9. doi: 10.3762/bjoc.9.330.

Abstract

The four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in the functionalized morpholinium or piperidinium 2-pyrrolidinon-3-olates in the presence of p-toluenesulfonic acid.

Keywords: benzothiazole; domino reaction; electron-deficient alkyne; multicomponent reaction; pyrrolidinone.