Synthesis of pyrazine-phosphonates and -phosphine oxides from 2H-azirines or oximes.
[reaction: see text] Tetrasubstituted pyrazines containing two phosphonate groups 2 in positions 2 and 5 and trisubstituted pyrazines containing a phosphonate 5 or a phosphine oxide group 7 in position 2 are obtained by thermal treatment of 2H-azirine-2-phosphonates 1 and -phosphine oxides 6. These pyrazines can also be prepared from beta-ketoxime tosylates 9 and 10 or from oxime derived from phosphine oxide 11.
Palacios
Francisco
F
Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain. qoppagaf@vc.ehu.es
Ochoa de Retana
Ana María
AM
Gil
José Ignacio
JI
López de Munain
Rafael
R
D001389:Azirines / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis*; D010091:Oximes / Q000737:chemistry*; D010766:Phosphorylation; D011719:Pyrazines / Q000138:chemical synthesis*
D001389:Azirines; D007202:Indicators and Reagents; D063065:Organophosphonates; D010091:Oximes; D011719:Pyrazines