Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy

Christopher Hulme, Liang Ma, Marie Pierre Cherrier, Joseph J. Romano, George Morton, Celine Duquenne, Joseph Salvino, Richard Labaudiniere

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

This communication reveals a novel application of the so-called convertible isonitriles for the solution/solid phase generation of γ-lactam analogues. Use of tethered N-BOC aldehydes in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3-step, 1-pot procedure') affords γ-lactams in good yield. The UDC (Ugi/De-BOC/Cyclize) strategy, coupled with a convertible isonitrile, is now feasible from all three substitution sites of the Ugi product. A conceptually novel approach, combining a bi-functional precursor with a post-condensation modification to give fused lactam-ketopiperazines, is also revealed. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1883-1887
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number12
DOIs
StatePublished - Mar 18 2000
Externally publishedYes

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Lactams
Aldehydes
Condensation
Solid solutions
Substitution reactions
Communication

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy. / Hulme, Christopher; Ma, Liang; Cherrier, Marie Pierre; Romano, Joseph J.; Morton, George; Duquenne, Celine; Salvino, Joseph; Labaudiniere, Richard.

In: Tetrahedron Letters, Vol. 41, No. 12, 18.03.2000, p. 1883-1887.

Research output: Contribution to journalArticle

Hulme, C, Ma, L, Cherrier, MP, Romano, JJ, Morton, G, Duquenne, C, Salvino, J & Labaudiniere, R 2000, 'Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy', Tetrahedron Letters, vol. 41, no. 12, pp. 1883-1887. https://doi.org/10.1016/S0040-4039(00)00052-6
Hulme, Christopher ; Ma, Liang ; Cherrier, Marie Pierre ; Romano, Joseph J. ; Morton, George ; Duquenne, Celine ; Salvino, Joseph ; Labaudiniere, Richard. / Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 12. pp. 1883-1887.
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