Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines

被引：11

作者：

Feng, Yadong ^{[1
,2
]}

Liu, Ying ^{[1
]}

Fu, Qi ^{[1
]}

Zou, Zhongai ^{[1
]}

Shen, Jinhai ^{[1
]}

Cui, Xiuling ^{[2
]}

机构：

[1] Xiamen Huaxia Univ, Coll Environm & Publ Hlth, Xiamen 361024, Peoples R China

[2] Huaqiao Univ, Engn Res Ctr Mol Med, Key Lab Fujian Mol Med,Minist Educ, Key Lab Xiamen Marine & Gene Drugs,Sch Biomed Sci, Xiamen 361021, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Benzoquinone imines; Ferrocene-initiated; Radical process; Benzoquinone; Amines; QUINOLINE N-OXIDES; C-H AMIDATION; QUINONE-IMIDES; IN-VITRO; SULFAMIDATION; EMBELIN; ALKYNES; BONDS;

D O I：

10.1016/j.cclet.2019.09.026

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ferrocene-initiated radical reaction of benzoquinone with amines has been successfully developed for the direct access to diaminobenzoquinone imines in high yields, in which the commercially available and cheap ferrocene was employed as a radical initiator and TBHP was used as an oxidant. Moreover, this reaction could be achieved with low loading of ferrocene (0.5 mol%). This protocol is highly efficient with good substrate tolerance and provides a new approach for the construction of benzoquinone imines with potential pharmaceutical interest. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：733 / 735

页数：3

共 56 条

[1] A practical access to acyl radicals from acyl hydrazides [J].

Bath, S ;

Laso, NM ;

Lopez-Ruiz, H ;

Quiclet-Sire, B ;

Zard, SZ .

CHEMICAL COMMUNICATIONS, 2003, (02) :204-205

[2] Acyl hydrazines as precursors to acyl radicals [J].

Braslau, R ;

Anderson, MO ;

Rivera, F ;

Jimenez, A ;

Haddad, T ;

Axon, JR .

TETRAHEDRON, 2002, 58 (27) :5513-5523

[3] A small molecule targeting the multifactorial nature of Alzheimer's disease [J].

Cavalli, Andrea ;

Bolognesi, Maria Laura ;

Capsoni, Simona ;

Andrisano, Vincenza ;

Bartolini, Manuela ;

Margotti, Elisa ;

Cattaneo, Antonino ;

Recanatini, Maurizio ;

Melchiorre, Carlo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (20) :3689-3692

[4]

Chao P., 2019, ORG LETT, V7, P2081

[5] I2-Mediated Iodization/[3+2] Cycloaddition/Nucleophilic Addition Tandem Reaction: Synthesis of Polyheterocycles Bearing Furoquinoline and Maleimide [J].

Du, Sidong ;

Pi, Chao ;

Wan, Ting ;

Wu, Yangjie ;

Cu, Xiuling .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1766-1770

[6] Ir-catalyzed regiospecific mono-sulfamidation of arylquinazolinones [J].

Feng, Yadong ;

Zhang, Zhenyue ;

Fu, Qi ;

Yao, Qiuhong ;

Huang, Huabin ;

Shen, Jinhai ;

Cui, Xiuling .

CHINESE CHEMICAL LETTERS, 2020, 31 (01) :58-60

[7] Ferrocene-Initiated Oxidative Cyclization of Benzaldehyde with Alkyne: New Strategy to Substituted Indenones [J].

Feng, Yadong ;

Zhang, Hong ;

Yu, Yunliang ;

Yang, Lei ;

Cui, Xiuling .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (16) :2740-2744

[8] Iridium-catalysed direct sulfamidation of quinazolinones [J].

Feng, Yadong ;

Li, Yudong ;

Yu, Yunliang ;

Wang, Lianhui ;

Cui, Xiuling .

RSC ADVANCES, 2018, 8 (16) :8450-8454

[9] SYNTHESIS OF EMBELIN, RAPANONE AND RELATED QUINONES BY PEROXIDE ALKYLATION [J].

FIESER, LF ;

CHAMBERLIN, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (01) :71-75

[10] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

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