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Beilstein J. Org. Chem. 2009, 5, No. 44, doi:10.3762/bjoc.5.44
Graphical Abstract
Scheme 1: Brominations of 6H-1,2-oxazines. a) Br2, Et2O, −30 °C, 2 h. b) Et3N, −30 °C to r.t., overnight.
Scheme 2: Chlorinations of 6H-1,2-oxazines. a) Cl2, Et2O, −30 °C. b) Et3N, −30 °C to r.t.
Scheme 3: Suzuki-couplings of 4-bromo-6H-1,2-oxazines. a) ArB(OH)2, Pd(PPh3)4, Na2CO3, toluene, 80 °C, 3 h.
Scheme 4: Sonogashira-couplings of 4-bromo-6H-1,2-oxazines. a) PdCl2(PPh3)2, CuI, Et3N, toluene, r.t., 6–20 h....
Scheme 5: Sonogashira-couplings of 4,5-dibromo-6H-1,2-oxazines. a) PdCl2(PPh3)2, CuI, Et3N, toluene, r.t., 4 ...
Scheme 6: Preparation of trisubstituted pyridine derivatives: a) BF3·OEt2, CH2Cl2, −78 °C to r.t., overnight.