4.4 Article

Chemistry of andrographolide: formation of novel di-spiropyrrolidino and di-spiropyrrolizidino-oxindole adducts via one-pot three-component [3+2] azomethine ylide cycloaddition

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 12, Pages 1585-1588

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.01.052

Keywords

Andrographolide; Azomethine ylide; Dipolar cycloaddition; Dispiro-oxindole; 2D NMR

Funding

  1. Council of Scientific and Industrial Research, Government of India [Project-0009]
  2. CSIR

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A facile synthesis of novel di-spiro compounds has been achieved via 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to the conjugated double bond of andrographolide. When the amino acid was changed from sarcosine to L-proline, the product formation took a different course as determined by 2D NMR and X-ray crystallographic analysis. (C) 2010 Elsevier Ltd. All rights reserved.

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