10.1007/s11178-008-2003-x

Abstract

Multicomponent heterocyclization of aliphatic amides with H 2 S and CH 2 O (1:3:2) in water-organic solvent mixture in the presence of BuONa led to the formation of 1,3,5-dithiazinane in high yield (30-95%) and with high selectivity (100%). Under these conditions benzamide gave 3,5-dibenzoyl-1,3,5-thiadiazinane in 74% yield, whereas due to ortho-effect the acetylsalicylamide with H 2 S and CH 2 O in a system BuOH-H 2 O without BuONa formed N-acetylsalicyloyl-1,3,5-dithiazinane (80%). Heterocyclization of α-aminosuccinic acid monoamide depending on the H 2 S and CH 2 O concentration occurred either at one or both NH 2 yielding respectively mono-or bisdithiazinanes.