Heteroaromatization with sulfonamido phenyl ethanone, part I: Synthesis of novel pyrrolo[2,3-D]pyrimidine and pyrrolo[3,2-E][1,2,4]triazolo[1,5-C] pyrimidine derivatives containing dimethylsulfonamide moiety

Abstract

4-(5-Amino-4-cyano-1-p-tolyl-1H-pyrrol-3-yl)-N,N-dimethyl- benzenesulfonamide (4) was prepared and converted to several pyrrolo[2,3-d]pyrimidin-5-yl)-N,N-dimethyl-benzenesulfonamide derivatives (5,7,9, and 13). Cyclocondensation of 13 with different electrophilic carbon reagents afforded several 4-(N,N-dimethylaminosulfonylphenyl)]pyrrolo[3,2-e][1, 2,4]triazolo[1,5-c]-pyrimidine derivatives (14-17,19, and 20); IR, 1HNMR, and mass spectra of the newly synthesized compounds were recorded. Most of the obtained compounds were screened against Gram-positive and Gram-negative bacteria and fungi, for which some of these derivatives gave promising results.