Domino Construction of Benzoxazole-Derived Sulfonamides via Metal-Free Denitrogenation of 5‑Iodo-1,2,3-triazoles in the Presence of SO2 and Amines

A straightforward domino approach to assemble benzoxazole-derived sulfonamides has been developed. The method is based on annulation-induced in situ generation of diazo compounds from readily available 2-(5-iodo-1,2,3-triazolyl)­phenols, followed by metal-free denitrogenative transformation upon the...

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Veröffentlicht in:Journal of organic chemistry 2021-04, Vol.86 (8), p.5639-5650
Hauptverfasser: Gevondian, Avetik G, Kotovshchikov, Yury N, Latyshev, Gennadij V, Lukashev, Nikolay V, Beletskaya, Irina P
Format: Artikel
Sprache:eng
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Zusammenfassung:A straightforward domino approach to assemble benzoxazole-derived sulfonamides has been developed. The method is based on annulation-induced in situ generation of diazo compounds from readily available 2-(5-iodo-1,2,3-triazolyl)­phenols, followed by metal-free denitrogenative transformation upon the action of 1,4-diazabicyclo[2.2.2]­octane bis­(sulfur dioxide) (DABSO) and amines. The protocol is operationally simple and features a broad substrate scope, furnishing a library of target compounds in generally good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00115