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

Article Subject:

Chemistry

KeyWords:

Antibacterial, Antifungal, Deprotection, Dichloro Phosphoryl Carbamates, Pyrazole

Download PDF:

C H. Lakshmi praveena et al, The Experiment, 2015.,Vol. 30(3), 1991-2001