Facile synthesis of 1-aminoisoquinolines via the tandem reactions of 2-alkynylbenzaldoximes with isothiocyanates

被引：21
|
作者：
Li, Wenhai [1 ]
Wang, Yue [2 ]
Lu, Tao [2 ,3 ]
机构：
[1] China Pharmaceut Univ, Sch Basic Sci, Dept Phys Chem, Nanjing 211198, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Sch Basic Sci, Lab Mol Design & Drug Discovery, Nanjing 210009, Jiangsu, Peoples R China
[3] China Pharmaceut Univ, Sch Basic Sci, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 34期
基金：
中国国家自然科学基金;
关键词：
1-Aminoisoquinoline; Tandem reaction; Silver triflate; Isothiocyanate; 2-Alkynylbenzaldoxime; ISOQUINOLINE-N-OXIDES; LONG-LIVED CATALYSTS; ARYL CHLORIDES; IN-VIVO; BIOLOGICAL EVALUATION; ANTITUMOR AGENTS; BOND FORMATION; LIGANDS; DERIVATIVES; CYCLIZATION;
D O I：
10.1016/j.tet.2012.06.030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new, concise, and efficient route for the synthesis of 1-aminoisoquinolines in good to excellent yields is described; this involves the reaction of 2-alkynylbenzaldoximes and isothiocyanates, which is catalyzed by silver triflate in dichloromethane, at room temperature. This transformation involves tandem 6-endo cyclization, [3+2] cycloaddition, and subsequent rearrangement. The simple operational protocol provides a cost-effective, diversity-oriented route to 1-aminoisoquinolines under neutral, mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6843 / 6848
页数：6
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