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 8 条

[1] 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
[2] 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
[3] 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
[4] 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
[5] Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA′BC sequential four-component reaction and their application to 2-arylquinoline synthesis
Ribelles, Pascual
Sridharan, Vellaisamy
Villacampa, Mercedes
Teresa Ramos, Ma
Carlos Menendez, J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (04) : 569 - 579
[6] A mild catalyzed imino Diels-Alder reaction for the synthesis of N-(2-(o-tolyl)-1,2,3,4-tetrahydroquinoline-4-yl)formamide derivatives as regulators of Quorum Sensing in Pseudomonas aeruginosa
Maza, Leidy J. Garcia
Florez, Dayanna F. Orosco
Salgado, Arturo Rene Mendoza
Rosales, Wendy
Mendoza-Torres, Evelyn
Melendez, Carlos Mario
RESULTS IN CHEMISTRY, 2023, 6
[7] Synthesis of 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-ones from Anilines and N-Vinyl Pyrrolidin-2-one Through Imino Diels-Alder Reaction Using 4-Nitro Phthalic Acid as Catalyst
Srinivasa, Aswathanarayana
Mahadevan, Kittappa M.
Hulikal, Vijaykumar
SYNTHETIC COMMUNICATIONS, 2009, 39 (01) : 93 - 101
[8] A Convenient Procedure for the Synthesis of New α-Pyridinyl-Substituted 7H-Indeno[2,1-c]quinoline Derivatives Based on a Three-Component Imino Diels-Alder Reaction
Kouznetsov, Vladimir V.
Romero Bohorquez, Arnold R.
Astudillo Saavedra, Luis
SYNTHESIS-STUTTGART, 2009, (24): : 4219 - 4225

← 1 →