Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin)

Christopher Hulme, Liang Ma, N. Vasant Kumar, Paul H. Krolikowski, Andrew C. Allen, Richard Labaudiniere

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

This communication reveals a novel application of resin bound α-amino acids coupled with the UDC (Ugi/DeBOC/cyclize) strategy. Reaction with either N-BOC-α-amino aldehydes or N-BOC anthranilic acids and subsequent acid treatment allows the preparation of highly pure and diverse arrays (approx. 10000 in size) of 1,4-benzodiazepines (Wang resin) and ketopiperazines (hydroxymethyl resin), respectively. Notable for the benzodiazepine series of compounds are the five potential points of diversity available from this two-step protocol. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1509-1514
Number of pages6
JournalTetrahedron Letters
Volume41
Issue number10
DOIs
StatePublished - Mar 4 2000
Externally publishedYes

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ortho-Aminobenzoates
Benzodiazepines
Aldehydes
Resins
Amino Acids
Acids
Communication
Bz-423
Wang resin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin). / Hulme, Christopher; Ma, Liang; Kumar, N. Vasant; Krolikowski, Paul H.; Allen, Andrew C.; Labaudiniere, Richard.

In: Tetrahedron Letters, Vol. 41, No. 10, 04.03.2000, p. 1509-1514.

Research output: Contribution to journalArticle

Hulme, Christopher ; Ma, Liang ; Kumar, N. Vasant ; Krolikowski, Paul H. ; Allen, Andrew C. ; Labaudiniere, Richard. / Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin). In: Tetrahedron Letters. 2000 ; Vol. 41, No. 10. pp. 1509-1514.
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