Brønsted Acid Triggers [6/7+1] Cascade Cyclization by N-Alkyl Amine C(sp3)-N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine

被引：1

作者：

Yin, Lu ^{[1
]}

Zhang, Zhou ^{[1
]}

Huang, Shuntao ^{[1
]}

Wang, Zhuoyu ^{[1
]}

Huang, Chao ^{[1
,2
]}

机构：

[1] Yunnan Minzu Univ, Sch Chem & Environm, Key Lab Biomass Green Chem Convers Yunnan Prov Edu, Yunnan Key Lab Chiral Funct Subst Res & Applicat, Kunming 650504, Peoples R China

[2] Yunnan Minzu Univ, Natl & Local Joint Engn Res Ctr Green Preparat Tec, Kunming 650504, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 18期

基金：

中国国家自然科学基金;

关键词：

BOND ACTIVATION; ALLYLIC AMINES; NS5B; INHIBITORS; DISCOVERY; INDOLE; SITE;

D O I：

10.1021/acs.joc.4c01827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and N-alkyl amines. The substrate and acidic additives were employed to cleave the C(sp(3))-N bond as a one-carbon synthon for C-C and C-O coupling, thus facilitating the [n + 1] cascade cyclization reaction, which enabled the construction of seven- and eight-membered N,O-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated N-alkyl amine 12 examples) and utilization of natural products (2 examples).

引用

页码：13629 / 13640

页数：12

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