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

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