Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Christopher Hulme, Liang Ma, Joseph J. Romano, George Morton, Sheng Yuh Tang, Marie Pierre Cherrier, Steve Choi, Joseph Salvino, Richard Labaudiniere

Research output: Contribution to journalArticle

61 Scopus citations

Abstract

This communication reveals novel applications of the CO2/MeOH reagent combination coupled with the UDC (Ugi/DeBOC/Cyclize) strategy. The Ugi five component condensation (5CC) affords carbamate protected amino-amides in good yield. When one of the supporting reagents employed in the Ugi reaction possesses a tethered amino-BOC protected functional group, subsequent acid treatment and proton scavenging results in rapid cyclization to cyclic ureas. Additionally, treatment of the 5CC product with base affords hydantoins in good yield, representing a novel and short approach to this class of molecule.

Original languageEnglish (US)
Pages (from-to)1889-1893
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number12
DOIs
StatePublished - Mar 18 2000
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Hulme, C., Ma, L., Romano, J. J., Morton, G., Tang, S. Y., Cherrier, M. P., Choi, S., Salvino, J., & Labaudiniere, R. (2000). Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction. Tetrahedron Letters, 41(12), 1889-1893. https://doi.org/10.1016/S0040-4039(00)00053-8