One-Pot Synthesis of Benzodiazepines through RuII-Catalyzed Regioselective [5+2] Annulation of N-Aryl Amidines with Alkynyl Cyclobutyl Acetates

被引：3

作者：

Shen, Jian ^{[1
,2
]}

Cui, Bo ^{[1
,2
]}

Huang, Junwei ^{[1
,2
]}

Lin, Shenghui ^{[2
]}

Cui, Xiuling ^{[1
,2
]}

机构：

[1] Huaqiao Univ, Engn Res Ctr Mol Med, Key Lab Precis Med & Mol Diag Fujian Univ, Sch Biomed Sci,Key Lab Fujian Mol Med,Key Lab Xiam, Xiamen 361021, Peoples R China

[2] Huaqiao Univ, Sch Biomed Sci, Quanzhou 362021, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 13期

关键词：

5+2] Cyclization; Alkynyl cyclobutyl acetates; Benzodiazepines; N-Aryl amidines; Ruthenium catalysis; C-H ACTIVATION; RING-CLOSING METATHESIS; BOND ACTIVATION; RH(III)-CATALYZED SYNTHESIS; DIVERGENT COUPLINGS; IMIDAMIDES; STRATEGY; ACCESS; DERIVATIVES; CYCLIZATION;

D O I：

10.1002/ejoc.202300064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient strategy to construct benzo[d][1,3]diazepines via selective C-H bond activation of N-aryl amidines and coupling with alkynyl cyclobutyl acetates was achieved successfully by Ru-II-catalyzed [5+2] cyclization. This protocol features excellent regioselectivity, wide substrate tolerance, mild reaction conditions, which might be potentially applied in the discovery of lead compounds for the developing new drugs.

引用

页数：4

共 49 条

[1] Synthesis of 1,3-Benzodiazepines through [5+2] Annulation of N-Aryl Amidines with Propargylic Esters
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