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) andchloro 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.
Issue
The Experiment 2015
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KeyWords:
Antibacterial, Antifungal, Deprotection, Dichloro Phosphoryl Carbamates, Pyrazole