7666-52-6Relevant academic research and scientific papers
Studies on Wallach's Imidazole Synthesis
Benincori, Tiziana,Brenna, Elisabetta,Sannicolo, Franco
, p. 675 - 680 (2007/10/02)
The reaction of the N-benzylamides of N-heterocyclic carboxylic acids 3 and 6-9 with phosphorus pentachloride affords heterocondensed imidazoles 4 and 10-14 by a scheme reminiscent of Wallach's imidazole synthesis starting from N,N'-dialkyloxamides.Kinetic and labelling experiments are described which support a mechanism involving nitrile ylide species and allow a better understanding of the Wallach reaction.The limiting parameter for the formation of heteroanellated imidazoles is the electron availability of the heterocyclic ring.
