N-sulfonylbenzotriazoles as advantageous reagents for C-sulfonylation.
[Structure: see text]. Reactions of readily available N-(alkyl-, aryl-, and heteroarylsulfonyl)benzotriazoles 3a-h with diverse nitriles, reactive heteroaromatics, alkylheteroaromatics, sulfones, and esters produced alpha-cyanoalkyl sulfones 5a-i, sulfonylheteroaromatics 7a-e, alpha-(sulfonylalkyl)heterocycles 9a-f, alpha-sulfonylalkyl sulfones 11a-g, and esters of alpha-sulfonyl acids 14a-c, respectively, in synthetically useful to excellent yields. The results represent the first examples of the successful application of sulfonylazoles for C-sulfonylation.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Abdel-Fattah
Ashraf A A
AA
Vakulenko
Anatoliy V
AV
Tao
Hui
H
D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
D013450:Sulfones; D013451:Sulfonic Acids; D014230:Triazoles