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A one-pot, three-component regiospecific synthesis of dispiropyrrolidines containing a thiophenone ring via 1,3-dipolar cycloaddition reactions of azomethine ylides

Moghaddam, F. M ; Sharif University of Technology | 2013

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  1. Type of Document: Article
  2. DOI: 10.1016/j.tetlet.2013.03.023
  3. Publisher: 2013
  4. Abstract:
  5. The synthesis of new dispiropyrrolidines containing a thiophenone ring has been achieved by a one-pot, three-component 1,3-dipolar cycloaddition reaction. Unsaturated thiophenone dipolarophiles were reacted with azomethine ylides, generated in situ from sarcosine and cycloketone derivatives (isatin, ninhydrin, acenaphthoquinone), to produce the corresponding cycloadducts in good yields (70-90%). The cycloaddition reaction was found to be highly regio- and diastereoselective
  6. Keywords:
  7. 1,3-Dipolar cycloaddition ; Azomethine ylide ; Dispiropyrrolidine ; Spiro oxindole ; Three-component reaction ; Acenaphthoquinone ; Dispiropyrrolidine derivative ; Isatin ; Ninhydrin ; Pyrrolidine derivative ; Quinone derivative ; Sarcosine ; Thiophene derivative ; Thiophenone dipolarophile derivative ; Unclassified drug ; Cycloaddition ; One pot synthesis ; One pot three component regiospecific synthesis
  8. Source: Tetrahedron Letters ; Volume 54, Issue 20 , May , 2013 , Pages 2520-2524 ; 00404039 (ISSN)
  9. URL: http://www.sciencedirect.com/science/article/pii/S0040403913004048