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Synthesis of new 3-[4-(N-alkyl-amino)phenyl)-4-(methanesulphonyl)phenyl]-5H-furan-2-one of expected antiinflammatory activity

Khaled R.A.Abdellatif, Mohamed A.Abdelgawad, Nermeen A.Helmy

A condensation-cyclization reaction of a 4-[N-alkyl-N-(tertbutyloxycarbonyl) amino]phenylacetic acid (12a-b) with 2-bromo-4- (methylsulphonyl)acetophenone (6) in the presence of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene afforded 4-[4-(methanesul phonyl)phenyl]-3-[4-(N-alkyl-N-tert-butyloxy carbonyl)amino)phenyl]-5Hfuran- 2-ones (13a-b) which upon reaction with HCl–saturated methanol gave non-protected furanones (14a-b). Subsequent reaction of the furanone (14a) 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 (15).