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N‐Sulfonylamines are generated and in situ reacted with 3‐dialkylamino‐2H‐azirines to give N‐sulfamoyl‐acrylamidines. The magnetic nonequivalence of prochiral groups in the 1H NMR spectrum suggests an axially chiral structure, which is supported by density‐functional theory calculations. Base‐induced cyclization occurs readily to give 1,2,6‐thiadiazine derivatives.
N-Sulfonylamine 2c was generated from the corresponding sulfamoyl chloride 1c at - 78°C by triethylamine-induced dehydrohalogenation or from the novel precursor 5 with a phthalimidyl leaving group at room temperature. Trapping of 2c from either source with 3-trimethylsiloxy-1,3-butadiene (3) gave the expected [2+4] cycloadduct 4. However, the reaction of N-sulfonyl-alkylamines 2 with 2-aza-1,3-dienes...
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