N-to-C Transmutations of Nitrogen-Containing Heterocycles

Abstract

Skeletal editing is an emerging area of research that has captivated chemists, as it entails the development of methods to modify molecules with a degree of precision that existing tools do not allow for. With the prevalence of nitrogen-containing heterocycles in drug molecules, techniques to edit such compounds in a small number of steps is of particular interest. This project reports a procedure that effects an N-to-C replacement with the use of a methyl phenyl sulfoxide and provides a library of substrates on which this transformation is successful. Overall, this “transmutation” necessitates that stabilizing functional groups such as alkenes or substituted benzenes be attached to the nitrogen-containing heterocycle. The project also reports efforts to test the N-to-C conversion using substituted sulfoxides, which would enable the transfer of complex alkyl chains to the edited molecule.