The Synthesis Of Cyano-containing Compounds Via Radical Process Initiated By Tert-butyl Nitrite

The radical reactions can be used to construct C-N,C-O and C-S bonds and are applied in various fields of organic chemistry.This paper focuses on the synthesis of cyanoformamide and cyanoquinoxalinone derivatives via radical process initiated by tert-butyl nitrite,and consists of the three parts:?1?The synthesis of nitrile compounds and quinoxalinones were summarized and analysed in detail.?2?The radical reaction of trifluoropropanamide to cyanoformamide initiated by tert-butyl nitrite via C-CF₃ bond cleavage and nitrogenation was studied.This method had the merits of excellent tolerance of functional groups and various trifluoropropanamides can proceed smoothly,giving cyanoformamide derivatives in moderate to good yields.Importantly,the construction of the nitrile group via new C-C single bond cleavage and nitrogenation cascades was established.?3?The synthesis of quinoxalinones via one-pot tandem nitrosation/cyclization of N-aryl cyanoacetamides initiated by tert-butyl nitrite has been developed.This convenient and efficient reaction afforded quinoxalin-2-ones in moderate to good yields and provided a new route for the nitrosation of some acid-sensitive substrates using tert-butyl nitrite as the nitroso group source.