Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole-Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines

被引：3

作者：

Titov, Gleb D. ^{[1
]}

Bunev, Alexander S. ^{[2
]}

Urusova, Svetlana V. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Rostovskii, Nikolai V. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia

[2] Togliatti State Univ, Med Chem Ctr, Tolyatti 445020, Russia

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 37期

基金：

俄罗斯科学基金会;

关键词：

DIVERGENT SYNTHESIS; 1,3-DIAZEPINES; ISOMERIZATION; ISOXAZOLES;

D O I：

10.1021/acs.orglett.4c02588

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A double dearomatization of dyads consisting of 1-sulfonyl-1,2,3-triazoles and 3-aryl-5-methoxyisoxazoles was applied for the efficient synthesis of nonfused 1H-1,3-diazepines. The plausible mechanism of the cascade reaction includes transformation of the 1,2,3-triazole to rhodium azavinyl carbene, the Z-selective hydride shift to form the 1-azabuta-1,3-diene moiety, rhodium-catalyzed ring contraction of the isoxazole to azirine, and pseudopericyclic four-atom ring expansion of the azirine. The synthetic utility and antiproliferative activity of the 1,3-diazepines obtained have been demonstrated.

引用

页码：7828 / 7833

页数：6

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