Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates

被引：26

作者：

Omar, Mohamed A. ^{[1
]}

Conrad, Juergen ^{[1
]}

Beifuss, Uwe ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

来源：

TETRAHEDRON | 2014年 / 70卷 / 35期

关键词：

Copper; Chromenes; Imidazobenzothiazines; Quinazolines; Domino reaction; ONE-POT SYNTHESIS; DIHYDROFOLATE-REDUCTASE; PNEUMOCYSTIS-CARINII; CASCADE SYNTHESIS; C-N; DERIVATIVES; INHIBITORS; DISCOVERY; APOPTOSIS; BROMIDES;

D O I：

10.1016/j.tet.2014.06.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with beta-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5682 / 5695

页数：14

共 50 条

[41] A New Route for the Synthesis of Trichloromethyl-1H-Benzo[d]imidazole and (1,2,3-Triazol)-1H-Benzo[d]imidazole Derivatives via Copper-Catalyzed N-Arylation and Huisgen Reactions
Nematpour, Manijeh
CURRENT ORGANIC CHEMISTRY, 2025, 29 (07) : 591 - 598
[42] Efficient and Direct Route to 5-Iodo-4 H -Quinoxalines via Copper-Catalyzed Double C-N Arylations of 1,2,3-Triiodoarenes: Potential Application towards 5-Substituted 4 H -Quinoxalines
Al-Zoubi, Raed M.
Al-Jammal, Walid K.
Shkoor, Mohanad
Bani-Yaseen, Abdulilah D.
Ferguson, Michael J.
SYNTHESIS-STUTTGART, 2024, 56 (23): : 3680 - 3686
[43] Synthesis of fused benzo [4,5]imidazo[1,2-a]pyrimidin-2-yl)methanone derivatives using copper-catalyzed aerobic oxidation via tandem approach
Kotla, Siva
Parang, Keykavous
Tiwari, Rakesh
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[44] Diversified Synthesis of 2-(4-Oxo[1,2,3]triazolo[1,5-a]quinoxalin-5(4H)-yl)acetamide Derivatives through Ugi-4-CR and Copper-Catalyzed Tandem Reactions
An, Yu
He, Huan
Liu, Tiantian
Zhang, Yong
Lu, Xiaoyun
Cai, Qian
SYNTHESIS-STUTTGART, 2017, 49 (17): : 3863 - 3873
[45] Copper-catalyzed [4+2] annulation reaction of β-enaminones and aryl diazonium salts without external oxidant: synthesis of highly functionalized 3H-1,2,4-triazines via homogeneous or heterogeneous strategy
Ding, Qifeng
Li, Mingrui
Sun, Yiming
Yu, Yang
Baell, Jonathan B.
Huang, Fei
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03) : 457 - 463
[46] Copper-Catalyzed Tandem Reactions of 2-Iodobenzamides with Sodium Azide: An Efficient Synthesis of [1,2,3] Triazolo[1,5-a][1,4]-benzodiazepin-6(5H)-ones
Chen, Wanli
Li, Haitao
Gu, Xiaoling
Zhu, Yinghong
SYNLETT, 2015, 26 (06) : 785 - 790
[47] Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones through Copper-Catalyzed Tandem Reactions of N-(2-Haloaryl)propiolamides with Sodium Azide
Yan, Jiajie
Zhou, Fengtao
Qin, Dongguang
Cai, Tong
Ding, Ke
Cai, Qian
ORGANIC LETTERS, 2012, 14 (05) : 1262 - 1265
[48] Chemodivergent, multicomponent domino reactions in aqueous media: L-proline-catalyzed assembly of densely functionalized 4H-pyrano[2,3-c]pyrazoles and bispyrazolyl propanoates from simple, acyclic starting materials
Prasanna, Pitchaimani
Perumal, Subbu
Menendez, J. Carlos
GREEN CHEMISTRY, 2013, 15 (05) : 1292 - 1299
[49] A Highly Selective Synthesis of (E)-11-Arylidenebenzo [4′,5′] thieno [2′,3′: 4,5] Pyrimido [2,1-a] Isoindol-13(1H)-ones via Copper-Catalyzed Sonogashira Coupling and Hydroamination
He, Heng
Wang, Zhen-Xu
Zhang, Mei-Mei
Liu, Jian-Quan
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (08)
[50] Synthesis of Chromeno[2,3-d]imidazol-9(1H)-ones via Tandem Reactions of 3-lodochromones with Amidines Involving Copper-Catalyzed C-H Functionalization and C-O Bond Formation
Sheng, Jia
Chao, Bo
Chen, Hong
Hu, Youhong
ORGANIC LETTERS, 2013, 15 (17) : 4508 - 4511

← 1 2 3 4 5 →