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Title
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Experimental and theoretical approaches to [1,5]-prototropic generation of an azomethine ylide and a 1,3-dipolar cycloaddition for novel spiropyrrolidine oxindoles synthesis
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Type
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JournalPaper
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Keywords
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Spiropyrrolidine oxindol, Azomethine ylide, 1,3-Dipolar cycloaddition, DFT calculation, [1,5]-H shift
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Abstract
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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 (DFT) 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.
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Researchers
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Saeid Yeganegi (Fourth Researcher), Kamal Alimohammadi (Third Researcher), Mahshid Hamzehloueian (Second Researcher), Yaghoub Sarrafi (First Researcher)
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