Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 5, Pages 1322-1329Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001505
Keywords
1,2-benzothiazine; C H activation; iridium catalysis; mechanochemistry; rhodium catalysis; sulfonimidamide
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Funding
- Alexander von Humboldt Foundation (AvH research award)
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Two different protocols were presented for the preparation of three-dimensional aza-analogues of 1,2-benzothiazine 1,1-dioxides from sulfonimidamides. The first method involves a rhodium-catalyzed annulation reaction to produce 4-unsubstituted benzothiazine derivatives, while the second method utilizes an iridium catalyst under solvent-free mechanochemical conditions to obtain products with 3,4-disubstituted thiazine rings.
Three-dimensional aza-analogues of 1,2-benzothiazine 1,1-dioxides have been prepared from sulfonimidamides. Two different protocols are presented. The first is a rhodium-catalyzed annulation reaction with alpha-sulfonyloxyketones leading to 4-unsubstituted benzothiazine derivatives. By selective bromination with NBS the heterocyclic ring can further be functionalized. In the second approach, an iridium catalyst is applied under solvent-free mechanochemical conditions providing products with 3,4-disubstituted thiazine rings from diazoketo esters and diazoketo sulfones.
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