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Synthesis 2004(2): 237-240
DOI: 10.1055/s-2003-44386
DOI: 10.1055/s-2003-44386
PAPER
© Georg Thieme Verlag Stuttgart · New York
The Formation of β-Lactam Derivatives through the Reaction of Dibenzoylacetylene and Aryl Isocyanates in the Presence of Trivalent Phosphorus Nucleophiles
Further Information
Received
27 August 2003
Publication Date:
18 December 2003 (online)
Publication History
Publication Date:
18 December 2003 (online)
Abstract
An effective route to novel β-lactams is described. This involves reaction of dibenzoylacetylene and phenyl isocyanate or phenylsulfonyl isocyanate in the presence of trivalent phosphorus nucleophiles.
Key words
triphenylphosphine - trialkyl phosphates - dibenzoylacetylene - aryl isocyanate - β-lactams
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1a
Durckheimer W.Blumbach J.Lattrell R.Scheunemann KH. Angew. Chem., Int. Ed. Engl. 1985, 24: 180 -
1b
Chu DTW.Plattner JJ.Katz L. J. Med. Chem. 1996, 39: 3853 -
1c
Chemistry and Biology of β-Lactam Antibiotics
Morin RB.Gorman M. Academic Press; New York: 1982. - 2
Moricioni EJ.Mazzocchi PH. J. Org. Chem. 1966, 31: 1372 - 3
Mukerjee AK.Shivastava RC. Synthesis 1973, 327 - 4
Recent Progress in the Synthesis of Anitbiotics
Luckacs G.Ohno M. Springer; Berlin: 1990. p.565 - 5
Skattebol L.Jones ERH.Whiting MC. Org. Synth., Coll. Vol. 4 Wiley; New York: 1963. p.792-794 - 6
Bowden K.Heilbron IM.Jones ERH.Weedon BC. J. Chem. Soc. 1946, 39 - 7
Yavari I.Alizadeh A. Tetrahedron 2001, 57: 9873 - 8
Yavari I.Alizadeh A. Tetrahedron Lett. 2003, 44: 2877 - 9
Hudson HR. The Chemistry of Organophosphorus Compounds: Primary Secondary and Tertiary Phosphines and Heterocyclic Organophosphorus (III) Compounds Vol. I: Wiley; New York: 1990. p.386-472 - 10
Engel R. Synthesis of Carbon-Phosphorus Bonds CRC Press; Boca Raton, FL: 1988. - 11
Cadogan JIG. Organophosphorus Reagents in Organic Synthesis Academic Press; New York: 1979. - 12
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863 - 13
Kolodiazhynyi OI. Russ., Chem. Rev. 1997, 66: 225-254 - 14
Tebby JC. In Phosphorus-31 NMR Spectroscopy in Stereochemical AnalysisVerkade JG.Quin LD. VCH Publishers; Weinheim: 1987. Chap. 1. p.1-60 - 15
Breitmaier E.Voelter W. Carbon-13 NMR Spectroscopy 3rd Ed.: VCH; New York: 1990. p.250