Preparation of a 990-member chemical compound library of hydantoin- and isoxazoline-containing heterocycles using multipin technology

Kyung Ho Park, Juerg Ehrler, Heinz Spoerri, Mark J. Kurth

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The development of a useful chemistry for the construction of polyfunctional heterocycles - first through solution and solid phase (resins) and then library production via SynPhase crowns - is reported. Bead-based synthetic work was done on Merrifield resin where treatment with benzylamine in the presence of DBU followed by reaction with 4-chloromethylbenzoyl chloride afforded amide-linked resin 9. Finally, TFA-NH2-polystyrene macro crowns were derivatized with 4-(hydroxymethyl)benzoic acid to afford pin 14 which was coupled with Boc-protected amino acid 2 in the presence of DIC to deliver pin 15. Deprotection and reaction with phenyl isocyanate afforded urea functionalized pin 17 which underwent 1,3-dipolar cycloaddition reaction to give pin 19. Finally, compound 20 was obtained with moderate diastereoselectivity (20:21::8:1) by the reaction of pin 19 with a catalytic amount of Et3N.

Original languageEnglish (US)
Pages (from-to)171-176
Number of pages6
JournalJournal of Combinatorial Chemistry
Volume3
Issue number2
DOIs
StatePublished - Mar 2001

Fingerprint

Hydantoins
Small Molecule Libraries
Chemical compounds
Crowns
Preparation
Resins
Technology
Dacarbazine
Benzoic Acid
Cycloaddition
Polystyrenes
Cycloaddition Reaction
Amides
Libraries
Macros
Urea
Chlorides
Amino Acids
Chemistry
Merrifield resin

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Discrete Mathematics and Combinatorics
  • Drug Discovery

Cite this

Preparation of a 990-member chemical compound library of hydantoin- and isoxazoline-containing heterocycles using multipin technology. / Park, Kyung Ho; Ehrler, Juerg; Spoerri, Heinz; Kurth, Mark J.

In: Journal of Combinatorial Chemistry, Vol. 3, No. 2, 03.2001, p. 171-176.

Research output: Contribution to journalArticle

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