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Synfacts 2009(6): 0606-0606  
DOI: 10.1055/s-0029-1216704
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Synthesis of Pyrano[2,3-c]pyrazoles

Contributor(s): Victor Snieckus, Johnathan Board
A. Shaabani, A. Sarvary, A. H. Rezayan, S. Keshipour
Shahid Beheshti University, Tehran, Iran
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

A three-component reaction of isocyanides, symmetrical dialkylacetylene dicarboxylates, and 1-phenyl-1H-pyrazol-5(4H)-one to give substituted pyrano[2,3-c]pyrazoles is described. A mechanism is proposed, whereby the alkyne is sequentially attacked through Michael addition of the isocyanide and pyrazolone to give a keteneimine, which is then further attacked by the pyrazolone to give the observed products. Although this mechanism is plausible, no evidence for it was presented by the authors.