Reactions of N-Sulfinylamines with Carbodiimides

概要

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N-Sulfinylsulfonamides 1a, b reacted with carbodiimides 2 to give the 1,2-cycloadducts, 3-imino-1,2,4-thiadiazetidin-1-oxides 3, which were readily thermolyzed to sulfonylcarbodiimides 4 and N-sulfinylamines 5. The alkaline or acidic hydrolysis of the cycloadducts 3a, b, d in ethanol gave the corresponding 1,3-disubstituted-2-p-toluenesulfonylguanidines 6a, b, d in good yields. Reduction of 3a by the Raney Ni produced similarly 6a in 87% yield. Reactions of N-sulfinylacylamides 1c, d with 2 led to the formation of an oily mixture of the 1,2-cycloadducts, 3-imino-4-acyl-1,2,4-thiadiazetidin-1-oxides 7 and the 1,4-cycloadducts, 5-imino-1,2,4,6-thiaoxadiazines 8. Thermal decomposition of the mixture gave 5, isocyanates 9, nitriles 10, and amides 13 as major products.
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