Some reactions of 1-alkyl-1,2,3,4-tetrahydropyridines with organic azides. Synthesis of 1-alkylpiperidylidene-2-sulfonamides

The 1,3-dipolar cycloaddition reaction of 1-substituted-1,2,3,4-tetrahydropyridines 4a-d with organic azides 5 afforded the respective 1-substituted-piperidylidene-2-sulfonamides 6 . In contrast, the reaction of (E)-1-(1-propenyl)-1,2,3,4-tetrahydropyridine ( 4e ) with 4-chlorobenzenesulfonyl azide yielded 6m as well as 1-(4-chlorophenyl)sulfonimine-1,2,3,4-tetrahydropyridine ( 7 ) arising from addition of the azide to the (E)-1-(1-propenyl) substituent of 4e .