Preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via phosphorus oxychloride-mediated cyclization of aminoureas

Rebecca E Deasy; Catherine N Slattery; Anita R Maguire; Douglas P Kjell; Mai Khanh N Hawk; Jung Min Joo; Rui Lin Gu; Humphrey Moynihan

doi:10.1021/jo500360k

Preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via phosphorus oxychloride-mediated cyclization of aminoureas

J Org Chem. 2014 Apr 18;79(8):3688-95. doi: 10.1021/jo500360k. Epub 2014 Mar 28.

Authors

Rebecca E Deasy¹, Catherine N Slattery, Anita R Maguire, Douglas P Kjell, Mai Khanh N Hawk, Jung Min Joo, Rui Lin Gu, Humphrey Moynihan

Affiliation

¹ Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork , Cork, Ireland.

PMID: 24641629
DOI: 10.1021/jo500360k

Abstract

The novel preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via the cyclization of (2-aminopyridin-3-yl)urea and (2-aminophenyl)urea substrates in the presence of phosphorus oxychloride is described. This methodology is demonstrated for a range of urea substrates with aminoimidazole products obtained in good yields and with excellent levels of purity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aminopyridines / chemical synthesis*
Aminopyridines / chemistry
Benzimidazoles / chemical synthesis*
Catalysis
Cyclization
Imidazoles / chemical synthesis*
Imidazoles / chemistry
Molecular Structure
Urea / analogs & derivatives*
Urea / chemical synthesis
Urea / chemistry

Substances

(2-aminophenyl)urea
(2-aminopyridin-3-yl)urea
Aminopyridines
Benzimidazoles
Imidazoles
Urea
2-aminobenzimidazole