Novel heterocycles. 4. Synthesis of the pyrido[2,3-c]-1,2-thiazine ring system

The reaction of 2-chloronicotinonitrile with N-methylmethanesulfonamide and subsequent treatment with base furnished the novel pyrido2,3-c]-1,2-thiazine ring system 7 . Spectrally, it was determined that the predominant tautomer in solution was the 4-amino form 7a . Acidic hydrolysis of 7 furnished the 4-oxo tautomer 8b , compound 8b was alkylated on oxygen with 1-bromopentane in the presence of sodium hydride. Reaction of 8b with isocyanates occurs at the 3 position to produce carboxanilides 10 . Spectral characteristics of these compounds are also discussed.