Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

N-H insertion reactions of primary ureas: The synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

authors

  • Lee, S. H.
  • Yoshida, K.
  • Matsushita, H.
  • Clapham, B.
  • Koch, G.
  • Zimmermann, J.
  • Janda, Kim

publication date

  • December 2004

journal

  • Journal of Organic Chemistry  Journal

abstract

  • Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoketones cyclize readily in the presence of acid to yield the corresponding imidazolones that can be further derivatized by N-alkylation with alkyl, allyl, and benzyl halides. Alternatively, the imidazolones were treated with phosphorus oxybromide to form the corresponding 2-bromoimidazoles that were further functionalized using a Suzuki coupling reaction.

subject areas

  • Azo Compounds
  • Catalysis
  • Cyclization
  • Imidazoles
  • Molecular Structure
  • Rhodium
  • Urea
scroll to property group menus

Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo048353u

PubMed ID

  • 15575764
scroll to property group menus

Additional Document Info

start page

  • 8829

end page

  • 8835

volume

  • 69

issue

  • 25

©2021 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support