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

Abstract

SummaryThe 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.

Ultrasound-assisted one-pot multi-component synthesis of 2-pyrrolidinon-3-olates catalyzed by Co3O4@SiO2core–shell nanocomposite

“…Furthermore, in order to show the merit of the present work toward the previous study (21), the model reaction was carried out to compare the results with previous conditions (Table 1, entry 5).…”

“…A plausible mechanism for the synthesis of pyrrolidinon-3-olate derivatives using Co 3 O 4 @SiO 2 nanocomposites has been shown in Scheme 3, based on the previous study (21). In general, the Co 3 O 4 @SiO 2 can act as a Lewis acid in order to increase the electrophilicity of the carbonyl group of the aldehydes and intermediates.…”

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

“…The applicability of this intermediate was shown by synthesizing functionalized 2-pyrrolidinones 368 and morpholinium/piperidinium 2-pyrrolidinon-3-olates 369 via the four-component reaction of 2-aminobenzothiazole 3b, aromatic aldehydes 4, acetylenedicarboxylate 362 and piperidine/morpholine 366. 220 Firstly, the Huisgen 1,4-dipole is obtained by mixing acetylenedicarboxylate 362 and piperidine/morpholine 366 at room temperature in ethanol, and then the reaction is further conducted with the remaining reactants toward the target compounds at moderate temperature. The reaction was stirred for two days to get both products in satisfactory yields.…”