87273-74-3Relevant articles and documents
S-PHENACYLATION OF 6-METHYL-4-OXO-2-THIO-2,3-DIHYDRO-4H-1,3-OXAZINE AND THE RING TRANSFORMATION OF THE S-PHENACYLATED COMPOUND
Sasaki, Tadashi,Ito, Eikoh,Asai, Koji
, p. 1089 - 1097 (2007/10/02)
1,3-oxazine 1 reacted with phenacyl bromide in water using sodium hydroxide as a base to give S-phenacylated derivative 2, but the homogeneous conditions such as NaH in THF or NaOMe in methanol caused the base-induced cycloreversion of 1, resulting in the formation of thiocyanate 3.For the purpose of the intramolecular transformation to pyrimidine-fused heterocycle 11, 2 was treated with ammonia in refluxing ethanol, but gave amidamine 6 while 8 was obtained with ammonium acetate in refluxing acetic acid.Although the direct ring closure failed, the target 11 was finally synthesized by the cyclodehydration of ketamide 7 with phosphorus pentoxide at 250 deg C.