Collect. Czech. Chem. Commun. 1985, 50, 357-364

α-Trichloromethylsulfonyl-5-nitro-2-furaldehydes, a new type of SH-group uncouplers and intermediates in the synthesis of 5-nitro-2-furylarylnitrilimines

Adolf Jurášeka, Jaroslav Kováča, Radoslav Palovčíkb and Ľuboš Mazaga

a Department of Organic Chemistry
b Department of Physical Chemistry, Slovak Institute of Technology, 812 37 Bratislava


Trichloromethylsulfonyl-5-nitro-2-furaldehyde 4-X-phenylhydrazones I (X = H, CH3, Cl, CN, NO2, COOC2H5) were obtained by reacting 4-X-phenyldiazonium salts with 5-nitrofurfuryltrichloromethyl sulfone. These compounds react with diazomethane and trimethylamine to give the corresponding N-methylated derivatives and nitrilimines, respectively, the latter under elimination of trichlorosulfinic acid. The hydrazone-diaziridine tautomerism was studied by 1H, 15N, and 13C NMR methods; also the IR and UV spectra of the compounds synthesized are discussed. All hydrazones showed a very strong effect on the stimulation of mitochondria respiration and constitute a new type of SH-group uncouplers acting already in a 10-8 mol l-1 concentration.