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Iodine-Mediated Oxidative N–N Bond Formations Providing Fused 1,2,3,5-Thiatriazole Derivatives from N -Pyridinyl Sulfonimidamides

Chandan Chittapriya Sahu, Shulei Pan, Yijie Hu, Kari T. Rissanen and 1 more

Organic Letters | Oct 6, 2026

Abstract

Abstract

Abstract An iodine-mediated oxidative annulation of N-pyridyl sulfonimidamides is reported, providing access to 2-substituted [1,2,3,5]thiatriazolo[3,4-a]pyridine 2-oxides through intramolecular N–N bond formation. This transition metal-free process offers a concise entry to bench-stable, highly heteroatom-rich sulfur(VI) heterocycles. In addition, divergent cyclizations during the preparation of alkyl sulfonimidamide precursors afford structurally distinct sulfur(IV) thiadiazole derivatives. The results of radical-trapping experiments suggest a pathway via an N-centered radical leading to cyclization followed by oxidative aromatization.

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Chandan Chittapriya Sahu

first | RWTH Aachen University | ORCID 0009-0002-1085-2496

Shulei Pan

middle | RWTH Aachen University

Yijie Hu

middle | RWTH Aachen University

Kari T. Rissanen

middle | University of Jyväskylä | ORCID 0000-0002-7282-8419

Carsten Bolm

last | RWTH Aachen University | ORCID 0000-0001-9415-9917

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Citation

BibTeX

@article{Sahu2026Iodine,
  title = {Iodine-Mediated Oxidative N–N Bond Formations Providing Fused 1,2,3,5-Thiatriazole Derivatives from N -Pyridinyl Sulfonimidamides},
  author = {Chandan Chittapriya Sahu and Shulei Pan and Yijie Hu and Kari T. Rissanen and Carsten Bolm},
  journal = {Organic Letters},
  year = {2026},
  doi = {10.1021/acs.orglett.6c03874},
  url = {https://doi.org/10.1021/acs.orglett.6c03874}
}

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