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Synfacts 2009(1): 0024-0024
DOI: 10.1055/s-0028-1087464
DOI: 10.1055/s-0028-1087464
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Three-Component Synthesis of Substituted Chromenes
G. Shanthi, P. T. Perumal*
Central Leather Research Institute, Chennai, India
Further Information
Publication History
Publication Date:
18 December 2008 (online)
Significance
Reported is the synthesis of 2-amino-3-cyano-4-allyl chromenes through the room-temperature three-component reaction of salicylaldehydes, malononitrile, and allyl bromides in the presence of sodium iodide and indium metal in water. A multi-stage mechanism is proposed, as shown, in which the malononitrile and aldehyde first undergo a Knoevenagel condensation, with subsequent phenolic OH attack to give the chromene. The resulting species undergoes reaction with an allylindium species to give the product. The reaction does not proceed well in organic solvents, or in the absence of sodium iodide.