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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c00115 |