The 1,3‐dipolarcycloaddition reaction of 1‐methyl‐1,2,3,4‐tetrahydropyridine (1) with organic azides 2 affords 1‐methylpiperidylidene‐2‐sulfon(cyan)amides 4 in high yield. The reaction proceeds via a 2,3,4,9‐tetrazabicyclo[4.3.0]non‐3‐ene intermediate. Acid hydrolysis of 4d gives rise to 1‐methyl‐2‐piperidone.
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Warren et al. (1982) studied this question.