0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. Variation 3: Reaction of 1,3-Oxazin-4-one with Thioamides

DOI: 10.1055/sos-SD-016-00463

von Angerer, S.Science of Synthesis, (200416482.

Treatment of 6-methyl-2-phenyl-4H-1,3-oxazin-4-one with various thioamides in the presence of sodium hydride affords 6-substituted 5-acetylpyridin-4-ols 356 in good yields whereas the use of the corresponding amides results in far lower yields (Scheme 190).[‌440‌] This ring conversion can formally be regarded as a CNCC+NC pyrimidine-forming reaction.

Meeeee 888 8-Meeeeeeeeee 8-Meeeeeeeeeeee-8-eee eeee 8-Meeeee-8-eeeeee-8M-8,8-eeeeee-8-eee eee Meeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeee-8-eeeeeeeeeeeeeee-8-ee (888, M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee ee MeM (8.888e, 88eeee) (eeee e 88% eeeeeeeeee ee MeM ee eeeeeee eee, eeeee eee eeee eeeeee eeeeeee eeeee ee eeeeeeeeeee eeee eeeeeeee MMM) eee eeeeeeeeeeeeeeeeeee (8.88e, 88eeee) ee MMM eee eeeee eeeeeeee eeee eeeeeeee e eeee ee 8-eeeeee-8-eeeeee-8M-8,8-eeeeee-8-eee (8.88e, 88eeee) ee MMM ee ee eeeee M8. Mee eeeeeee eee eeeeeee eee ee eeeeeeeeee 88e, eeeeeeeeeee eeee 88% ee MMe, eee eeee eeeeeee ee eeee ee ee eee/eeee eeeeeee. Mee eeeeeeeeeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee. Me eeeeeeeeee eeeeeeee ee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeee. Meeeeeeeeeeeeeeee ee eee eeeeeeee eeeeeee (88% MeMM) eeee eeeeeeeee eeeeeee; eeeee: 8.88e (88%); ee 888°M (eee).