Abstract

Synthesis characterization and antimicrobial activity of 6-nitro-1H-benzo[d] oxazol /thiazol-2-yl)methyl)-6-oxido-4,8-dihydro-1H-[1,3,2]dioxaphosphepino [5,6-c]pyrazole-6-yl)ureas/carboxamides

Author(s): C. H. Lakshmi Praveena, V. Esther Rani, Y. N. Spoorthy and L. K. Ravindranath

New novel derivatives of 1-(1-((5-nitrbenzo [d] oxazol-2-yl)methyl)-6-oxido-4,8-dihydro-1H- [1,3,2]dioxaphosphepino[5,6-c]pyrazol-6yl)-3(phenyl/p-tolyl/4-methoxy phenyl /4-chlorophenyl) ureas (8a-d as per scheme: I ) were Synthesized by condensation reaction of 1-((5-nitro benzo [d] oxazol-2-yl)methyl) -1H-pyraazole- 4,5-diyl) dimethanol (6) and (phenyl carbamoyl) phosphoric acid dichlorides 7(a-d). The synthon (6) was obtained by deprotection of isopropilidine group of 6, 6-dimethyl-1-((5-nitrobenzo[d]oxazol-2-yl) methyl-4, 8-dihydro-1H-[1, 3] dioxepino [5, 6-c] pyrazole (5). The synthon (5) was obtained by condensation reaction between 2-(6, 6-dimethyl- 4, 8-dihydro -1H-[1, 3] dioxepino [5, 6-c] pyrazole-1-yl) acetic acid (3) and 2-amino-nitrophenol. Similar procedures were adopted to prepare N-(1-((5-nitrobenzo [d] oxazol -2-yl) methyl)-6-oxido-4, 8-dihydro-1H-[1, 3, 2] dioxaphospheno [5,6-c] pyrazol-6-yl) morpholine/piper dine/4-methyl piperazine carboxamides (8e-g as per scheme: II). The synthesis of 1-(1-(benzo [d] thiazole-2-yl) methyl)-6-oxido-4,8-dihydro-1H- [1,3,2]dioxaphosphepino[5,6-c]pyrazol-6yl)-3(phenyl/p-tolyl/4-methoxyphenyl/4-chloro phenyl) ureas(12a-d as depicted in scheme:III) and N-(1-(benzo [d]thiazol-2-ylmethyl)-6-oxido-4, 8-dihydro-1H-[1, 3, 2] dioxaphosphepino [5.6-c] pyrazol-6-yl) morpholine / piperidine /4-methyl piperazinecarboxamides (12e-g as depicted in scheme:IV) were also carried out by the usage of similar synthetic procedures.

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