Catalyst-Controlled Regioselective Approach to 1-Aminoisoquinolines and/or 1-Aminoisoindolines through Aminative Domino Cyclization of 2-Alkynylbenzonitriles

被引：19
作者：
Reddy, Virsinha [1 ]
Jadhav, Abhijeet S. [1 ]
Anand, Ramasamy Vijaya [1 ]
机构：
[1] Indian Inst Sci Educ & Res IISER, Dept Chem Sci, Sect 81,Manauli PO, Sas Nagar 140306, Punjab, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 03期
关键词：
Amination; Heterocycles; Isoquinolines; Isoindolines; Domino reactions; LONG-LIVED CATALYSTS; ARYL CHLORIDES; ELECTROPHILIC CYCLIZATION; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; TANDEM REACTIONS; DESIGN; LIGANDS; ANTAGONISTS; 2-ALKYNYLBENZALDOXIMES;
D O I：
10.1002/ejoc.201501390
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-catalyzed regioselective approach towards the synthesis of 1-aminoisoquinolines and/or 1-aminoisindolines through aminative domino cyclization of 2-alkynylbenzonitriles with secondary amines has been developed under solvent-free conditions. It was found that the regioselectivity of the reaction was greatly influenced by the choice of the metal catalyst. Copper-based catalysts favored 6-endo-dig cyclization leading to 1-aminoisoquinolines, whereas other catalysts such as triflates of Zn, Ag, Bi, Sc and Yb favored the formation of 1-aminoisoindolines through 5-exo-dig cyclization.
引用
收藏
页码：453 / 458
页数：6
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