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Synthesis of new 1-[4-methane(amino)sulfonylphenyl)]-5-[4-(aminophenyl)]-3-trifluoromethyl-1H-pyrazoles

✍ Scribed by Khaled R. A. Abdellatif; Morshed A. Chowdhury; Edward E. Knaus

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
190 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A regiospecific cyclization‐dehydration reaction of a 1‐[(4‐(N‐alkyl‐N‐(tert‐butyloxycarbony)amino)‐phenyl]‐4,4,4‐trifluorobutane‐1,3‐done with a 4‐aminosulfonyl‐, or 4‐methylsulfonyl‐, phenylhydrazine hydrochloride in refluxing ethanol proceeded with simultaneous loss of the N‐tert‐butyloxycarbonyl protecting group to afford a group of 1‐(4‐methanesulfonylphenyl or 4‐aminosulfonylphenyl)‐5‐[4‐(N‐alkylaminophenyl)]‐3‐(trifluoromethyl)‐11__H__‐pyrazoles(6). Subsequent reaction of the pyrazole 6 (R^1^ = R^2^ = Me) with nitric oxide (40 psi) proceeded via a N‐methylamino‐N‐diazen‐1‐ium‐1,2‐diolate intermediate that undergoes protonation of the more basic diazen‐1‐ium‐1,2‐diolate N^2^‐nitrogen and then loss of a nitroxyl (HNO) species to furnish the N‐nitroso product 7.

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