1,2,3-Benzotriazine Synthesis by Heterocyclization of p‑Tosylmethyl Isocyanide Derivatives

1,2,3-Benzotriazine Synthesis by Heterocyclization of p‑Tosylmethyl Isocyanide Derivatives

An efficient methodology to form 4-alkoxy- and 4-aryloxybenzo­[d]­[1,2,3]­triazines via an intramolecular heterocyclization of 1-azido-2-[isocyano­(p-tosyl)­methyl]­benzenes under basic conditions has been developed. DFT calculations have been performed to further understand the mechanism of this he...

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Veröffentlicht in:Journal of organic chemistry 2023-10, Vol.88 (19), p.14131-14139
Hauptverfasser: Maqueda-Zelaya, Francisco, Aceña, José Luis, Merino, Estíbaliz, Vaquero, Juan J., Sucunza, David
Format: Artikel
Sprache:eng
Schlagworte:
benzene
organic chemistry
triazines
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Zusammenfassung:An efficient methodology to form 4-alkoxy- and 4-aryloxybenzo­[d]­[1,2,3]­triazines via an intramolecular heterocyclization of 1-azido-2-[isocyano­(p-tosyl)­methyl]­benzenes under basic conditions has been developed. DFT calculations have been performed to further understand the mechanism of this heterocyclization, which occurs in good to excellent yields with a broad scope.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01675