Synthesis of Polysubstituted 2-Aminoimidazoles via Alkene-Diamination of Guanidine with Conjugated α-Bromoalkenones

Sankar K. Guchhait*, Neha Hura and Archana P. Shah

*Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, SAS Nagar (Mohali), Punjab 160062, India, Email: skguchhaitniper.ac.in

S. K. Guchhait, N. Hura, A. P. Shah, J. Org. Chem., 2017, 82, 2745-2752.

DOI: 10.1021/acs.joc.6b03021

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Abstract

A step-economical access to polysubstituted aminoimidazoles via alkene vicinal C-N bonds formation of 2-bromo-2-alkenones with guanidine avoids a NH-protection/derivatization strategy. The reaction involves a tandem pathway of aza-Michael addition, S_N2, and a unique redox-neutral process and offers an excellent substrate scope.

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proposed mechanism

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Key Words

imidazoles, manganese(IV) oxide

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ID: J42-Y2017