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
收藏
页码：5682 / 5695
页数：14
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