Study of the effect of solvent and different Lewis acids in one pot multicomponent microwave assisted reaction for the chemoselective generation of 1.4-thiazepan-3-ones and 4-tiazolidinones.

ROMINA A. OCAMPO ; ALDANA A. QUIROGA; IGNACIO O. COSTILLA; FERNANDO J. LORENZO ; JUAN J. CALMELS ; DANIELA P. VILLAFAIN; SANDRA D. MANDOLESI ; NORMA B. D'ACCORSO

Basilea

Conferencia; The 21st International Electronic Conference on Synthetic Organic Chemistry; 2017

MDPI (Multidisciplinary Digital Publishing Institute)

With the aim of exploring the best reaction conditions for the diastereoselective synthesis of the 1,4-thiazepan-3-ones (4) and 4-thiazolidinones (5), we have studied the effect on solvent variation and the aggregation of AlCl3 and different zeolites as Lewis acid catalysts to the three-component microwave assisted reaction between 2,3:4,5-di-O-isopropylidene-β-D- arabino-hexos-2-ulo-2,6-pyranose (1), benzotiazole (3) and thioglycolic acid (2). Based on the results of previous studies of our group, we discuss here two microwave assisted methods: multicomponent reaction in the presence of the catalysts (Method A) and sequential reaction with generation of the corresponding intermediates and subsequent addition of the catalysts coordinated to thioglycolic acid (Method B).