Navigation

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.
16.12.2.2.3.3 Reaction of 1,3-Oxazin-4-ones with Thioamides

DOI: 10.1055/sos-SD-116-00063

von Angerer, S.Science of Synthesis Knowledge Updates, (20111282.

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-acetylpyrimidin-4-ols 479 in good yields, whereas the use of the corresponding amides results in far lower yields (Scheme 266).[‌634‌] This ring conversion can formally be regarded as a C–N–C–C + N–C pyrimidine-forming reaction.

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

Meeeeeeeeee 888

M8 Meeee (%) Mee
Me 88 [‌888‌]
Me 88 [‌888‌]
Me 88 [‌888‌]
Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

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

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

References