Experimental and theoretical approaches to [1,5]-prototropic generation of an azomethine ylide and a 1,3-dipolar cycloaddition for novel spiropyrrolidine oxindoles synthesis

被引:31
作者
Sarrafi, Yaghoub [1 ]
Hamzehloueian, Mahshid [1 ]
Alimohammadi, Kamal [2 ]
Yeganegi, Saeid [3 ]
机构
[1] Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
[2] Univ Payambare Aazam, Sari, Iran
[3] Univ Mazandaran, Fac Chem, Dept Phys Chem, Babol Sar 47416, Iran
关键词
Spiropyrrolidine oxindole; Azomethine ylide; 1,3-Dipolar cycloaddition; DFT calculation; 1,5]-H shift; DIELS-ALDER REACTION; DENSITY-FUNCTIONAL THEORY; POLAR 3+2 CYCLOADDITION; LEWIS-ACID CATALYST; IMINIUM ION ROUTE; TRANSITION STRUCTURES; CARBONYL-COMPOUNDS; REGIOSELECTIVE SYNTHESIS; POTENTIAL 1,3-DIPOLES; INPLANE AROMATICITY;
D O I
10.1016/j.molstruc.2012.04.013
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of spiropyrrolidine oxindoles was synthesized via a multicomponent 1,3-dipolar cycloaddition reaction of isatin, benzylamine and chalcone derivatives. The regio- and stereochemistry of the products were established by single crystal X-ray structure and spectroscopic techniques. The molecular mechanism of this cycloaddition has been investigated by means of a density functional theory (OFT) method. The energy path in preparing the azomethine ylide via a [1.5]-H shift in an iminium ion was evaluated. The regio- and stereoselectivity were explained on the basis of transition states stabilities, global and local reactivity indices of the reactants. The cycloaddition has been assumed to take place through one-step pathway in which two C-C bonds are formed in a nonsynchronous way. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:168 / 176
页数:9
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