A Facile Synthesis of Quinazolin-4(3H)-ones via Copper-Catalyzed One-Pot, Three-Component Tandem Reaction

被引：13

作者：

Dhiman, Shiv ^{[1
]}

Nandwana, Nitesh K. ^{[1
]}

Dhayal, Shreemala ^{[1
]}

Saini, Hitesh K. ^{[1
]}

Kumar, Dalip ^{[1
]}

Kumar, Anil ^{[1
]}

机构：

[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 26期

关键词：

Amination; copper catalyst; C-N coupling; quinazolin-4(3H)-ones; tandem reaction; three-component reaction; C-H AMIDATION; INTRAMOLECULAR DIRECT ARYLATION; BIOLOGICAL EVALUATION; 2,3-DISUBSTITUTED QUINAZOLINONES; 2-ARYL QUINAZOLINONES; DOMINO SYNTHESIS; N-HETEROCYCLES; ARYL HALIDES; BENZIMIDAZOLES; INHIBITORS;

D O I：

10.1002/slct.201701778

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and convenient one-pot, three-component tandem reaction has been developed for the synthesis of substituted quinazolin-4(3H)-ones using CuI/L-proline as catalytic system. A series of 35 quinazolin-4(3H)-ones was synthesized in good to high yield. The method involves copper-catalyzed double C-N coupling, reductive amination, condensation, cyclization and aerobic oxidation. Good functional group tolerance, mild reaction condition, readily available starting materials and user friendly procedure makes this protocol practically good and attractive method for the synthesis of quinazolin-4(3H)-ones.

引用

页码：8016 / 8019

页数：4

共 50 条

[11] One-Pot Three Component Synthesis of Quinazolin-4(3H)-One Derivatives: Investigation of Photophysical Properties and FRET Application toward Protein Lysozyme
Sarkar, Soumen
Mandal, Subhro
Pramanik, Animesh
POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (03) : 1896 - 1917
[12] Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
Hue Thi Buu Bui
Kiep Minh Do
Huy Tran Duc Nguyen
Hieu Van Mai
Thanh La Duc Danh
De Quang Tran
Morita, Hiroyuki
TETRAHEDRON, 2021, 98
[13] Synthesis of 2-Arylbenzothiazoles by Copper-Catalyzed One-Pot Three-Component Reactions in Water
Xu, Hualong
Luo, Chun
Li, Zhengkai
Xiang, Haifeng
Zhou, Xiangge
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (04) : 1207 - 1213
[14] Efficient Room-Temperature One-Pot Synthesis of 2-Amino-3-alkyl(3-aryl)quinazolin-4(3H)-ones
Lecoutey, Cedric
Fossey, Christine
Rault, Sylvain
Fabis, Frederic
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) : 2785 - 2788
[15] One-Pot Copper-Catalyzed Three-Component Synthesis of Quinoxalines by Condensation and C-N Bond Formation
Yuan, Hua
Li, Kangning
Chen, Yongxin
Wang, Yu
Cui, Jiaojiao
Chen, Baohua
SYNLETT, 2013, 24 (17) : 2315 - 2319
[16] Copper-catalyzed three-component reaction of pyrazol-3-ones (antipyrine), triarylbismuthines, and selenium: Synthesis of 4-selanylpyrazol-3-ones
Matsumura, Mio
Nakamura, Ayaka
Yanagida, Atsuki
Murata, Yuki
Yasuike, Shuji
TETRAHEDRON, 2023, 142
[17] Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
Foroumadi, Parham
Lotfi, Vahid
Mahdavi, Mohammad
Moghimi, Setareh
Soheiliza, Mehdi
Kianmehr, Ebrahim
Firoozpour, Loghman
Asadipour, Alj
Foroumadi, Alireza
HETEROCYCLIC COMMUNICATIONS, 2018, 24 (05) : 267 - 271
[18] Rhodium catalyzed three-component reaction of aldehyde, boronic acid, and sulfonamides: a facile one-pot synthesis of diarylmethylamines
Satyanarayana, Ponnam
Reddy, Ganapam Manohar
Maheswaran, Hariharasarma
Kantam, Mannepalli Lakshmi
TETRAHEDRON LETTERS, 2014, 55 (40) : 5439 - 5442
[19] Copper-catalyzed one-pot three-component thioamination of 1,4-naphthoquinone
Zeng, Fan-Lin
Chen, Xiao-Lan
He, Shuai-Qi
Sun, Kai
Liu, Yan
Fu, Rui
Qu, Ling-Bo
Zhao, Yu-Fen
Yu, Bing
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (09): : 1476 - 1480
[20] Molybdenum-mediated synthesis of quinazolin-4(3H)-ones via cyclocarbonylation using microwave irradiation
Roberts, Bryan
Liptrot, David
Luker, Tim
Stocks, Michael J.
Barber, Catherine
Webb, Nicola
Dods, Robert
Martin, Barrie
TETRAHEDRON LETTERS, 2011, 52 (29) : 3793 - 3796

← 1 2 3 4 5 →