Synthesis of N-Substituted 3-Chloro-2-azetidinones for 2, 4-diamino-6-hydroxy pyrimidin

Abstract

This search involved synthesis of several new N-Substituted -3-chloro-2-azetidinones which were known as a high medicinal effectiveness for 2, 4-Diamino-6-hydroxy pyrimidin in two steps. The first step included preparation Shiff bases (1-6) by condensation of 2, 4-Diamino-6-hydroxy pyrimidin with many substituted aldehydes(4-hydroxy benzaldehyde, 2-bromobenzaldehyde, 4-dimethyl amino benzaldehyde, 4-nitro benzaldehyde, salicylaldehyde, 4-chlorobenzaldehyde), then the second step included, preparation new six azetidinones compounds (7-12) by reaction of chloroacetylchloride with the prepared Schiff bases in the first step in the presence of triethylamine. The structures of synthesized compounds were- characterized by physical properties (FT-IR, UV and some of them by 1H-NMR, 13C-NMR spectroscopy) were recorded. Keywords: 2,4-diamino-6-hydroxypyrimidine, Schiff bases, azetidinones, synthesis Introduction Azetidinones, commonly known as β-lactams ,were well-known heterocyclic compounds among the organic and medicinal chemists[1] are the derivatives of azetidines, four membered with carbonyl group at 2nd position [2,3] .They are still most prescribed antibiotics used in medicine, also considered as an important contribution of science to humanity[4]. The most widely used antibiotics such as the penicillins, cepholosporins, carumonam, azetreonam, thienamycine and the nocadincins all contain β-lactams ring [5].