A practical synthesis of quinazolinones via intermolecular cyclization between 2-halobenzamides and benzylamines catalyzed by copper(I) immobilized on MCM-41

被引：13

作者：

Yan, Nan

You, Chongren

Cai, Mingzhong ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2019年 / 897卷

基金：

中国国家自然科学基金;

关键词：

Copper; Quinazolinone; Tandem reaction; Annulation; Heterogeneous catalysis; ONE-POT SYNTHESIS; C-N; TERMINAL ALKYNES; LIGAND-FREE; EFFICIENT; ARYL; DERIVATIVES; COMPLEXES; ARYLATION; HYDROGENATION;

D O I：

10.1016/j.jorganchem.2019.07.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The heterogeneous tandem N-arylation/oxidative CeH amidation of 2-halobenzamides and benzylamines was achieved in DMSO at 110 or 120 degrees C by using an MCM-41-immobilized L-proline copper(I) complex [MCM-41-L-Proline-CuBr] as the catalyst and air as the oxidant, yielding a variety of quinazolinone derivatives in good yields. The new MCM-41-L-Proline-CuBr catalyst can easily be prepared from commercially readily available and inexpensive reagents and recovered by filtration of the reaction mixture, and reused up to seven times with almost consistent activity. (c) 2019 Elsevier B.V. All rights reserved.

引用

页码：161 / 169

页数：9

共 24 条

[1] Practical Oxidative Homo- and Heterocoupling of Terminal Alkynes Catalyzed by Immobilized Copper in MCM-41
Xiao, Ruian
Yao, Ruiya
Cai, Mingzhong
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) : 4178 - 4184
[2] A practical access to 1,2-dicarbonyls via oxidation of alkynes catalyzed by gold(I) immobilized on MCM-41
Zeng, Jiajun
Li, Jianying
Huang, Bin
Li, Jiajia
Cai, Mingzhong
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2022, 976
[3] Novel α,α-difluorohomophthalimides via copper-catalyzed tandom cross-coupling-cyclization of 2-halobenzamides with a α,α-difluoro Reformatskii reagent
Pan, YJ
Holmes, CP
Tumelty, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12): : 4897 - 4900
[4] A practical synthesis of 2-aminobenzothiazoles via the tandem reactions of 2-haloanilines with isothiocyanates catalyzed by immobilization of copper in MCM-41
Xiao, Ruian
Hao, Wenyan
Ai, Jinting
Cai, Ming-Zhong
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 705 : 44 - 50
[5] An efficient heterogeneous cross-coupling of aryl iodides with diphenylphosphine catalyzed by copper (I) immobilized in MCM-41
Fang, Zhiqiang
Cai, Mingzhong
Lin, Yang
Zhao, Hong
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (08)
[6] A simple and green synthesis of diaryl sulfides catalyzed by an MCM-41-immobilized copper(I) complex in neat water
Cai, Mingzhong
Xiao, Ruian
Yan, Tao
Zhao, Hong
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 749 : 55 - 60
[7] Synthesis of 2-hydroxy-1,4-naphthoquinone derivatives via a three-component reaction catalyzed by nanoporous MCM-41
Shaabani, Soroush
Naimi-Jamal, Mohammad Reza
Maleki, Ali
[J]. DYES AND PIGMENTS, 2015, 122 : 46 - 49
[8] Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-one, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41
Tamoradi, Taiebeh
Ghadermazi, Mohammad
Ghorbani-Choghamarani, Arash
[J]. CATALYSIS LETTERS, 2018, 148 (03) : 857 - 872
[9] Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-one, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41
Taiebeh Tamoradi
Mohammad Ghadermazi
Arash Ghorbani-Choghamarani
[J]. Catalysis Letters, 2018, 148 : 857 - 872
[10] Heterogeneous gold(I)-catalyzed cyclization between ynals and amidines: An efficient and practical synthesis of 2,4-disubstituted pyrimidines
Jiang, Minhua
Nie, Quan
Cai, Mingzhong
[J]. SYNTHETIC COMMUNICATIONS, 2019, 49 (19) : 2488 - 2500

← 1 2 3 →