239124-59-5Relevant academic research and scientific papers
Studies on the reactivity of α-cyano-α-isocyanoalkanoates - Versatile synthons for the assembly of imidazoles
Bergemann, Marco,Neidlein, Richard
, p. 909 - 918 (2007/10/03)
The reactivity and the synthetic potential of α-cyano-α- isocyanoalkanoates 2 were investigated. Interestingly, reaction of 2 with alkoxides gave (alkoxy)(alkyl)imidazoles 5, whereas the analogous thiolates led to different products, namely substituted 4H-imidazoles 7, together with compounds 6, which formed by addition of thiolate to the isocyano group. Primary amines reacted, on one hand, in the same manner as thiolates to form of 4H-imidazoles 10, and, on the other hand, cleavage of the molecule to the proposed unstable aminoimidazole 8 and the carbamate 9 was observed. Secondary amines add selectively to the isocyano group to form compounds 11. Like simple isocyanides, α-cyano-α-isocyanoalkanoates 2 can be subjected to [4+1] cycloadditions and multicomponent reactions of the Passerini type. Mechanisms for the described reactions are discussed.
