Copper-catalyzed N-arylation of 1,2,4-oxadiazin-5(6H)-ones by diaryliodonium salts

Copper-catalyzed N-arylation of 1,2,4-oxadiazin-5(6H)-ones by diaryliodonium salts

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Parent link:Organic and Biomolecular Chemistry.— .— London: Royal Society of Chemistry
Vol. 23, iss. 17.— 2025.— P. 4217-4225
Altri autori: Presnukhina S. I. Sofia, Baykova S. O. Svetlana, Chukanova E. A. Elizaveta, Metalnikova N. M. Nadezhda Maksimovna, Baykov S. V. Sergey, Soldatova N. S. Nataliya Sergeevna, Postnikov P. S. Pavel Sergeevich, Boyarskiy V. P. Vadim
Riassunto:Herein, we developed a new synthetic approach for the preparation of N-arylated 1,2,4-oxadiazin-5(6H)-ones by direct arylation with diaryliodonium salts. The reaction with symmetrical diaryliodonium salts using CuI as a catalyst proceeded in toluene in the presence of DIPEA at 60 °C with the formation of the desired products in isolated yields of 46 to 97% (20 examples). The use of more readily available unsymmetrical diaryliodonium salts required higher reaction temperatures (up to 100 °C) to achieve similar yields. The only limitation observed in reaction was with an ortho-substituted iodonium salt. In all other cases, the developed approach allowed the preparation of a broad range of N-arylated 1,2,4-oxadiazin-5(6H)-ones under mild conditions utilizing a cheap and readily available catalyst
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Pubblicazione: 2025
Soggetti:
труды учёных ТПУ
электронный ресурс
Accesso online:https://doi.org/10.1039/D5OB00204D
Natura: Elettronico Capitolo di libro
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=680065

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