2005
Organo-phosphorus compounds
S 0080
Regioselective Synthesis of 4- and 5-Oxazole-phosphine Oxides and -phosphofrom 2H-Azirines and Acyl Chlorides. — Addition of acyl chlorides to phos02- 174 nates
phorylated azirines leads to N-acylated products which can undergo regioselective
ring-opening at C1 or C2 to afford vinylamides or vinylogous α-amidophosphorus
compounds. Base treatment of the latter provides a simple, mild, and convenient
approach to 5- and 4-phosphorylated oxazoles, respectively. Reaction of the phenyl
azirines (VIII) with acetyl chloride directly gives the oxazoles (IX). The products are
of synthetic and biological interest. — (PALACIOS*, F.; OCHOA DE RETANA, A.
M.; GIL, J. I.; ALONSO, J. M.; Tetrahedron 60 (2004) 40, 8937-8947; Dep. Quim.
Org., Fac. Farm., Univ. Pais Vasco, E-01080 Vitoria, Spain; Eng.) — Jannicke
2005