70205-72-0Relevant academic research and scientific papers
Copper-catalyzed N-aryl-β-enaminonitrile synthesis utilizing isocyanides as the nitrogen source
Kim, Seoksun,Hong, Soon Hyeok
, p. 1004 - 1012 (2015/03/30)
A novel synthetic protocol for N-aryl-β-enaminonitriles, which are useful building blocks for heterocycle synthesis, was developed using isocyanides as the nitrogen source. Using copper-catalyzed one-step reactions between isocyanides and benzyl cyanides under mild conditions, diverse N-aryl-β-enaminonitriles could be synthesized in excellent yields and with high atom-efficiency. N-Alkyl-β-enaminonitriles were also synthesized in good yields. A mechanism involving an imidoyl-copper intermediate was proposed based on mechanistic studies and previous reports. In addition, we demonstrated that a synthesized N-aryl-β-enaminonitrile could be utilized for the synthesis of a β-keto nitrile compound and 3-aminopyrazole.
Studies with enaminonitriles: Synthesis and chemical reactivity of 2-phenyl-3-piperidin-1-yl acrylonitrile under microwave heating
Salaheldin, Abdellatif M.,Alphy, Maryana K.
, p. 307 - 310 (2008/09/20)
(Chemical Equation Presented) Benzyl cyanide reacts with triethylorthoformate and piperidine in DMF solution to yield the title compound 2. This reacted with aromatic amines to yield either aminoacrylonitriles orquinoline depending on reaction conditions and substitution pattern on the aromatic amine. The reaction of compound 2 with hydrazine hydrate could only be effected in the microwave oven and resulted in the formation of aminopyrazole 7. Diazotization of 7 and coupling with an active methylene reagent afforded pyrazolo[5,1-c]-[1,2,4]triazine derivatives.
