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Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides

Shubhangi P. Bhoite, Ajay H. Bansode and Gurunath Suryavanshi*

*Chemical Engineering & Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India, Email:

S. P. Bhoite, A. H. Bansode, G. Suryavanshi, J. Org. Chem., 2020, 85, 14858-14865.

DOI: 10.1021/acs.joc.0c01358

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An efficient, safe, and environmentally friendly TBHP-mediated rearrangement of aryl/alkylidene malononitrile with anilines produces in situ HCN as the cyanide source for the synthesis of substituted α-aminonitriles and α-aminoamides in very good yields. This method features good functional group tolerance, and the in situ-generated HCN bypasses the use of an external cyanide source.

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proposed mechanism

Key Words

cyanation, amination, TBHP

ID: J42-Y2020