The Formation of β-Lactam Derivatives through the Reaction of Dibenzoyl­acetylene and Aryl Isocyanates in the Presence of Trivalent Phosphorus Nucleophiles

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

References

• 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 Analysis   Verkade 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