Mild and Simple Access to Diverse 4-Amino-substituted 2-Phenyl-1,2,3,4-tetrahydroquinolines and 2-Phenylquinolines Based on a Multicomponent Imino Diels-Alder Reaction

被引：11

作者：

Varma, P. Prabhakara ^{[1
]}

Sherigara, Bailure S. ^{[1
]}

Mahadevan, Kittappa M. ^{[2
]}

Hulikal, Vijaykumar ^{[3
]}

机构：

[1] Kuvempu Univ, Sch Chem Sci, Dept Postgrad Studies & Res Chem, Shankaraghatta, Karnataka, India

[2] Kuvempu Univ, Sch Chem Sci, Dept Chem, Shankaraghatta, Karnataka, India

[3] Bioorgan & Appl Mat Pvt Ltd, Bangalore, Karnataka, India

来源：

SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 15期

关键词：

Antimony trichloride; 2-phenylquinolines; tetrahydroquinoline; N-vinylcaprolactam; N-vinylpyrrolidin-2-one; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; TETRAHYDROQUINOLINES; QUINOLINES;

D O I：

10.1080/00397910903221035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of new 1-(2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones/azepan-2-one from N-vinyl caprolactam/N-vinylpyrrolidin-2-one and N-benzylideneaniline via the imino Diels-Alder reaction has been reported for the first time. Antimony(III) chloride has been shown to effectively catalyze imino-Diels-Alder reaction to afford both 2-phenylquinoline and 2-phenyl-1,2,3,4-tetrahydroquinolin derivatives in excellent yields at ambient temperature. The cis diastereoselectivity to give cis 2-phenyl-1,2,3,4-tetrahydroquinolines is also highlighted in this reaction.

引用

页码：2220 / 2231

页数：12

共 44 条

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