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REGIO- AND STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION REACTIONS BETWEEN ARYLIDENEACETONES AND STABILIZED AZOMETHINE YLIDES OBTAINED FROM NINHYDRIN AND INDENOQUINOXALINONES

Vladislav Yu. Korotaev, Alexey Yu. Barkov, Nikolay S. Zimnitskiy, Igor B. Kutyashev, Vyacheslav Ya. Sosnovskikh
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Abstract


Stabilized azomethine ylides, generated in situ from proline/sarcosine and ninhydrin or indenoquinoxalinones, underwent 1,3-dipolar
cycloaddition at the activated double bond of arylideneacetones, leading predominantly to endo-spiro adducts. These products formed as
a result of addition between the less substituted carbon atom of azomethine ylide and the most electrophilic site of the dipolarophile.

Keywords


arylideneacetones, spiropyrrolidines, spiropyrrolizidines, stabilized azomethine ylides, 1,3-dipolar cycloaddition.

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