K 2 CO 3 -Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage

We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves...

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Veröffentlicht in:Organic letters 2020-04, Vol.22 (8), p.3268-3272
Hauptverfasser: Pike, Ryan A S, Sapkota, Rishi R, Shrestha, Bijay, Dhungana, Roshan K, Kc, Shekhar, Dickie, Diane A, Giri, Ramesh
Format: Artikel
Sprache:eng
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Zusammenfassung:We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves the cleavage of one C(sp )-C(sp ) bond in 1,3-diketones and the formation of one carbon-nitrogen bond and four carbon-carbon bonds to construct both the aryl and pyrrole rings of the indole in one step.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01057