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SYNTHESIS OF NEW SPIROOXINDOLOPYRROLIDINES VIA THREE-COMPONENT REACTION OF ISATINS, α-AMINO ACIDS, AND (E)-3-ARYL-2-CYANOACRYLAMIDES OR (E)-3-ARYL-2-(4-ARYLTHIAZOL-2-YL)ACRYLONITRILES

Tetyana L. Pavlovska, Victoria V. Lipson, Svetlana V. Shishkina, Vladimir I. Musatov, Julia A. Nichaenko, Victor V. Dotsenko
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Abstract


A series of novel spirooxindolopyrrolidine derivatives has been prepared via a three-component 1,3-dipolar cycloaddition reaction of 2-oxindoleazomethine ylides generated in situ from isatin and sarcosine or valine with (E)-3-aryl-2-cyanoacrylamides or (E)-3-aryl-2-(4-arylthiazol-2-yl)acrylonitriles as dipolarophiles. To rationalize the observed regio- and stereoselectivity, calculations of the geometrical structures of all possible conformers and charge distribution in the reacting systems were performed.


Keywords


azomethine ylide; cyanoacrylamide; sarcosine; spiro[indoline-3,2'-pyrrolidin]-2-one; thiazoleacrylonitrile

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