Pike, R. A. S.; Sapkota, R. R.; Shrestha, B.; Dhungana, R. K.; Kc, S.; Dickie, D. A.; Giri, R. K2CO3-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage. Organic Letters 2020, 22, 3268-3272.
NOTES
Pike, Ryan A SSapkota, Rishi RShrestha, BijayDhungana, Roshan KKc, ShekharDickie, Diane AGiri, RameshengOrg Lett. 2020 Apr 2. doi: 10.1021/acs.orglett.0c01057.
Abstract
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(sp3)–C(sp2) 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.