Add time:08/24/2019         Source:sciencedirect.com

3-Diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (1) was made to react with arylalkyl- and arylazides 2. Cycloadducts 3, which could be isolated in some cases, afforded N-arylalkyl- or N-aryl-thiadiazabicyclo[3.1.0]hexene derivatives 4 through N2-elimination. Thermal rearrangements of N-aryl- and N-β-phenylethyl substituted compounds 4b-e, produced derivatives of 1,2-thiazete 1,1-dioxide 5, 1,2,6-thiadiazine 1,1-dioxide 6 and pyrazole 7. The reaction can be optimized to afford compounds 6 in synthetically useful yield. In the case of N-benzyl-thiadiazabicyclo[3.1.0]hexene derivative 4a the different substitution on the aziridine nitrogen produced a different reaction course, affording the thiadiazine derivative 6a and the pyrimidine derivative 8.

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