Article Subject
Chemistry
Abstract

New novel derivatives of Cyclopropyl/ Cyclohexyl Terahydro-2H-pyran-4-yl / Tetrahydro-2H-thiopyran-4-yl/perfluorophenyl(1-((5-(3-chloro-2-oxo - 4 - (pyridin - 3 - yl) azetadin - 1 - yl)-1,3,4-thiadiazol-2-yl)methyl-6-oxido-4,8-dihydro-1H-[1,3,2]dioxa phosphepino [5,6 - c] pyrazol-6 - yl)carbamates (7a-e as depicted in scheme)  were synthesized  from  condensation reaction of substituted dichlorophosphoryl carbamates  (6a – e) and 1 - (5 - ((4, 5 - bis (hydroxymethyl) -1H - pyrazol - methyl) - 1, 3, 4 - thiadiazol - 2 - yl) - 3-chloro - 4 - (pyridine -3 - yl) azetidin-  2 - one(5). The Synthon (5)was obtained by deprotection of  3 - chloro -1 - (5 - ((6, 6 - dimethyl - 4, 8 - dihydro - 1H -[1, 3]dioxepino[5, 6 - c] pyrazol -1 -  yl) -1, 3, 4 - thiadiazol - 2 - yl) - 4 - (pyidin - 3-yl) azetidin - 2 - one (4). Synthon (4) was prepared by the reaction between 5 - ((6, 6 - dimethyl - 4, 8 –dihydro -  1H - [1, 3] dioxepino [5, 6 - c] pyrazol - 1 - yl) methyl) - N - (pyridine  - 3 - ylmethylene) - 1, 3, 4 - thiadiazol - 2 - amine (3) and chloro acetyl chloride in presence of Et3N / Dioxane / POCl3 on   NaN3 / THF conditions under the temperature 100oC / 2-mecaptoacetic acid in presence of ZnCl2. The synthon (3) was obtained by condensation reaction between nicotinaldehyde (2) and 5 - ((6, 6 -  dimethyl - 4, 8 - dihydro - 1H - [1, 3]dioxepino [5, 6 - c] pyrazol - 1 - yl) methyl - 1, 3, 4 -  thiadiazol -2 - amine (1).  The products were characterized by spectral analysis (IR,                              1H- NMR,13C- NMR, 31P- NMR and elemental analysis). The newly synthesized compounds were subjected to various biological activities viz., antimicrobial.

Keywords
Antibacterial; Antifungal; deprotection; dichloro phosphoryl carbamates; Pyrazole.
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