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

[1] Transformations of 2-(α-furyl)-4-(2-oxopyrrolidinyl-1)-1,2,3,4-tetrahydroquinolines, cycloadducts of the imino Diels-Alder reaction:: A simple synthesis of new quinoline derivatives
Kouznetsov, Vladimir V.
Cruz, Uriel Mora
LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (09) : 699 - 702
[2] Practical one-pot procedure for the synthesis of 1,2,3,4-tetrahydroquinolines by the Imino-Diels-Alder reaction
Dehnhardt, Christoph M.
Espinal, Yomery
Venkatesan, Aranapkam M.
SYNTHETIC COMMUNICATIONS, 2008, 38 (05) : 796 - 802
[3] Imino Diels-Alder Reactions: Efficient Synthesis of 2-Aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by Antimony(III) Sulfate
Aswathanarayana Srinivasa
Kittappa M. Mahadevan
Vijaykumar Hulikal
Monatshefte für Chemie - Chemical Monthly, 2008, 139 : 255 - 259
[4] Imino Diels-Alder reactions:: Efficient synthesis of 2-aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by antimony(III) sulfate
Srinivasa, Aswathanarayana
Mahadevan, Kittappa M.
Hulikal, Vijaykumar
MONATSHEFTE FUR CHEMIE, 2008, 139 (03): : 255 - 259
[5] FeCl3-Catalyzed Synthesis of 2-Methyl-4-Substituted-1,2,3,4-Tetrahydroquinoline Derivatives by the Imino Diels-Alder Reaction
Chen, Ye
Lee, Yong Rok
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (07): : 2485 - 2488
[6] Imino Diels-Alder reaction - An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride
Kavitha, C. S.
Hosamani, K. M.
Harisha, R. S.
CANADIAN JOURNAL OF CHEMISTRY, 2010, 88 (05) : 443 - 452
[7] Mechanochemical milling promoted solvent-free imino Diels-Alder reaction catalyzed by FeCl3: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines
Tan, Ya-Jun
Zhang, Ze
Wang, Fang-Jian
Wu, Hao-Hao
Li, Qing-Hai
RSC ADVANCES, 2014, 4 (67): : 35635 - 35638
[8] Hydrogenation of ortho-nitrochalcones over Pd/C as a simple access to 2-substituted 1,2,3,4-tetrahydroquinolines
Patti, Angela
Pedotti, Sonia
TETRAHEDRON, 2010, 66 (30) : 5607 - 5611
[9] The first aza Diels-Alder reaction involving an α,β-unsaturated hydrazone as the dienophile:: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter
Sridharan, Vellaisamy
Perumal, Paramasivan T.
Avendano, Carmen
Menendez, J. Carlos
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (09) : 1351 - 1353
[10] One Pot Synthesis of Medicinally Important cis-2-Methyl-4-amino substituted-1,2,3,4-tetrahydroquinolines
Kiran, Kumar H. C.
Mahadevan, K. M.
Prabhakara, Varma P.
Srinivasa, A.
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (03) : 534 - 540

← 1 2 3 4 5 →