Condensation of acrylonitrile and aryl acetonitrile: construction of α-amino-β-cyano cyclohexene skeletons

• Published in: RSC advances Vol. 12; no. 46; pp. 2984 - 29843
• Main Authors: Zhang, Wei, Tang, Chuan-Su, Xiang, Shi-Qun
• Format: Journal Article
• Language: English
• Published: Cambridge Royal Society of Chemistry 18.10.2022; The Royal Society of Chemistry
• Subjects: Acetonitrile; Aromatic compounds; Chemistry; Cyclohexene; Room temperature
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d2ra04936h

A representative condensation of acrylonitrile and aryl acetonitrile has been reported for the synthesis of α-amino-β-cyano cyclohexene. The reaction was carried out mildly in an open environment at room temperature. The scope and versatility of the method have been demonstrated with 20 examples, containing highly active ethynyl groups. Further applications for 4-aminopyrimidine compounds were performed. A mechanism was proposed, involving Michael additions between acrylonitrile and aryl acetonitriles as well as intramolecular condensation. A condensation reaction between acrylonitrile and benzyl cyanide for the synthesis of α-amino-β-cyano cyclohexene was reported. The reaction could be carried out mildly with high atomic efficiency to build the cyclohexene skeleton.