Synthesis of some metal derivatives of azomethine group compounds containing Isoindoline-1,3-dione moiety and novel heterocyclic compounds of anticipated antimicrobial activity

Abstract

In this study, the hitherto unknown 6-amino-4-(2-chloro-5-nitrophenyl)-3-methyl-1, 4-dihydropyrano [2,3-c] pyrazole-5-carbonitrile 2a was synthesized. Both 2a and its 2,4-dichl-orophenyl derivative 2b were utilized as building blocks for the preparation of novel class of pyrazolo pyrano-[oxazines 3a-d and pyrimidinones 4a–d]. Also, compound 2a was used to prepare novel heterocycles compounds by reaction with some chemical reagents as formic acid gave pyrimidin-5(1H)-one 5, with sulfuric acid to hydrolysis the cyano group to amide one as in compound 6, with triethyl ortho formate yielded ethyl 4-(2-chloro-5-nitrophenyl)-5-cyano-3-methyl-1,4-dihydro- pyrano[2,3-c]pyrazol-6-ylimidoformate 7, which by reaction with hydrazine hydrate as 1,2-binucleophile yielded 3-amino pyranopyrimidine derivative 12 and with ammonium solution (NH4OH) gave the unexpected product 13. Also, on reacting compound 2a with acetic anhydride in pyridine yielded diacetyl derivative 9, and with benzoyl chloride in toluene afforded benzamide derivative 8 while its reaction with phenyl isocyanate and carbon disulfide led to produce urea derivative 10 and dithioic acid 11, respectively. The structures of the syn- thesized compounds were elucidated by spectral data and ele- mental analysis. Screening and evaluation of these products as antimicrobial agents showed that these compounds possess a potent activity.