A facile regioselective 1,3-dipolar cycloaddition protocol for the synthesis of new class of quinolinyl dispiro heterocycles

被引：21

作者：

Kumar, Gopal Senthil ^{[1
]}

Satheeshkumar, Rajendran ^{[1
]}

Kaminsky, Werner ^{[2
]}

Platts, James ^{[3
]}

Prasad, Karnam Jayarampillai Rajendra ^{[1
]}

机构：

[1] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India

[2] Univ Washington, Dept Chem, Seattle, WA 98195 USA

[3] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 40期

关键词：

1,3-Dipolar cycloaddition; Azomethine ylides; Quinolinyl dispiro heterocycles; Secondary orbital interaction; Non-covalent interaction; DIVERSITY-ORIENTED SYNTHESIS; MOLECULAR-ORBITAL METHODS; GAUSSIAN-TYPE BASIS; AZOMETHINE YLIDES; BIOLOGICAL EVALUATION; BASIS-SETS; APPROXIMATION; CONSTRUCTION; ENERGY;

D O I：

10.1016/j.tetlet.2014.08.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ from isatin and secondary amino acids with quinolinyl dipolarophiles in refluxing methanol afforded new class of quinolinyl dispiro heterocycles with multi hetero core units. The regio and stereochemistry of the product was unambiguously assigned by H-1, C-13, 2D NMR techniques and single crystal X-ray analysis. The structures of the compounds are stabilized through the presence of intermolecular hydrogen bonding and intramolecular non-covalent interactions. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5475 / 5480

页数：6

共 48 条

[1]

Bader R. F. W., 1994, ATOMS MOL QUANTUM TH

[2] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[3]

Biegler-König F, 2001, J COMPUT CHEM, V22, P545, DOI 10.1002/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO

[4]

2-Y

[5] KF/Al2O3 mediated 1,3-dipolar cycloaddition of azomethine ylides:: a novel and convenient procedure for the synthesis of highly substituted pyrrolidines [J].

Boruah, Monalisa ;

Konwar, Dilip ;

Das Sharma, Saikat .

TETRAHEDRON LETTERS, 2007, 48 (26) :4535-4537

[6] Generating diverse skeletons of small molecules combinatorially [J].

Burke, MD ;

Berger, EM ;

Schreiber, SL .

SCIENCE, 2003, 302 (5645) :613-618

[7] A planning strategy for diversity-oriented synthesis [J].

Burke, MD ;

Schreiber, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58

[8] EFFICIENT DIFFUSE FUNCTION-AUGMENTED BASIS SETS FOR ANION CALCULATIONS. III. THE 3-21+G BASIS SET FOR FIRST-ROW ELEMENTS, LI-F [J].

CLARK, T ;

CHANDRASEKHAR, J ;

SPITZNAGEL, GW ;

SCHLEYER, PV .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (03) :294-301

[9] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[10] Direct construction of novel dispiro heterocycles through 1,3-dipolar cycloaddition of azomethine ylides [J].

Dandia, Anshu ;

Jain, Anuj K. ;

Bhati, Dharmendra S. .

TETRAHEDRON LETTERS, 2011, 52 (41) :5333-5337

← 1 2 3 4 5 →