Solid-phase synthesis of linear ureas tethered to hydantoins and thiohydantoins

Adel Nefzi, Marcello Giulianotti, Long Truong, Somkit Rattan, John M. Ostresh, Richard A. Houghten

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

An efficient method for the solid-phase synthesis of hydantoins and thiohydantoins tethered to ureas, starting from a resin-bound amino acid, is presented. Following reduction of the amide with borane - THF, a second amino acid was selectively coupled to the primary amine followed by treatment of the secondary amine by an isocyanate to generate the corresponding urea. Hydantoin and thiohydantoin formation was achieved through the use of carbonyldiimidazole and thiocarbonyldiimidazole, respectively. Cleavage from the solid support using hydrogen fluoride, followed by extraction and lyophilization, provided the desired urea-linked heterocyclic compounds in good yield and high purity.

Original languageEnglish (US)
Pages (from-to)175-178
Number of pages4
JournalJournal of Combinatorial Chemistry
Volume4
Issue number2
DOIs
StatePublished - Mar 2002
Externally publishedYes

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