1258289-19-8Relevant articles and documents
Assembly of the bis(imidazolyl)propene core of nagelamides c and s by double grignard reaction
Jacobi, Nicolas,Lindel, Thomas
experimental part, p. 5415 - 5425 (2010/11/18)
As characteristic structural elements of several of the nonmonomeric pyrrole-imidazole alkaloids, l, l-bis(imidazolyl)propenes were assembled in a facile manner by double Grignard reaction of metalated imidazoles with saturated esters, followed by dehydration. The presence of nitrile functions or acryl esters in the electrophile component leads to competing reactions, whereas propargyl esters are tolerated. Introduction of 2-amino groups was possible via the corresponding dimethylsulfamoyl-protected 2-azidoimidazoles, which had to be deprotected prior to hydrogenation. NOESY-based analysis revealed preferred orientation of the imidazole 5positions towards the propenyl chain.