824399-34-0Relevant academic research and scientific papers
Synthesis of new 1-[4-methane(amino)sulfonylphenyl]-5-[4-(aminophenyl)]-3- trifluoromethyl-1H-pyrazoles
Abdellatif, Khaled R. A.,Chowdhury, Morshed A.,Knaus, Edward E.
experimental part, p. 1707 - 1710 (2009/09/08)
(Chemical Equation Presented) A regiospecific cyclization-dehydration reaction of a 1-[4-(N-alkyl-N-(tert-butyloxycarbonyl)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)-1H-pyrazoles (6). Subsequent reaction of the pyrazole 6 (R1 = R2 = 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 N2-nitrogen and then loss of a nitroxyl (HNO) species to furnish the N-nitroso product 7.
