Controllable Synthesis of N-Heterocycles via Hydride Transfer Strategy-Enabled Formal [5+1] and [5+2] Cyclizations

被引：22

作者：

Dong, Ying ^{[1
]}

Hu, Fangzhi ^{[1
]}

Wu, Huixin ^{[1
]}

Guo, Feng-Wei ^{[1
]}

Wang, Liang ^{[1
]}

Du, Feng-Yu ^{[1
]}

Li, Shuai-Shuai ^{[1
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 26卷 / 01期

基金：

中国国家自然科学基金;

关键词：

H BOND FUNCTIONALIZATION; TRANSFER/CYCLIZATION PROCESS; 1-BENZAZEPINES; INDOLES; AGENTS;

D O I：

10.1021/acs.orglett.3c03986

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Bronsted acid-controlled switchable synthesis of indoline-fused tetrahydroquinolines and indole-fused benzazepines was developed through hydride transfer-enabled formal [5 + 1] and [5 + 2] cyclization reactions from indoles and N-alkyl o-aminobenzoketones. Indoline, furanone, and tetrahydroquinoline hybridized pentacyclic products were unprecedentedly accessed via a cascade condensation/hydride transfer/dearomatization-cyclization/deethylation/nucleophilic addition process. In addition, the undeveloped hydride transfer-involved [5 + 2] cyclizations were also realized for direct construction of indole-fused benzazepines.

引用

页码：332 / 337

页数：6

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