Synthesis of novel anti-bacterial 2,1-benzothiazine 2,2-dioxides derived from methyl anthranilate

Abstract

A convenient ultrasound assisted synthesis of new anti-bacterial N-benzylidene-N'-(1-methyl-2, 2-dioxo-2,3-dihydro-1H-2?6-benzo[c][1,2]thiazin-4- ylidene)-hydrazines from methyl anthranilate is reported. Methyl anthranilate was reacted with methane sulfonyl chloride, followed by N-alkylation and subsequent base catalyzed cyclization. Hydrazinolysis of the cyclized products followed by their ultrasound mediated condensations with different benzaldehydes yielded the title compounds. Some of these compounds showed good anti-bacterial activity against Pseudomonas aeruginosa, Salmonella typhimurium and Staphylococcus aureus.