A novel heterocyclic compound. Synthesis and reactivities of an oxazolo[3,2-a]thieno[3,2-d]-pyrimidine derivative.
A practical preparation of 2,3-dihydro-5H-oxazolo[3,2-a]thieno[3,2-d]pyrimidin-5-one (2) from methyl 3-aminothiophene-2-carboxylate in two steps was developed. The addition reactions of various nucleophiles to 2 were investigated and oxazole-ring-opened compounds were produced (5, 6, 12, 13 and 14). Desulfurization reaction of 2 with Raney Ni gave an oxazolo[3,2-a]pyrimidine derivative (15). It was found that 2 showed potent anti-gastric secretion activity.
Fukumi
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H
Sugiyama
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Sakamoto
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T
D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000897:Anti-Ulcer Agents; D010080:Oxazoles; D011744:Pyrimidinones; C063359:2,3-dihydro-5H-oxazolo(3,2-a)thieno(3,2-d)pyrimidin-5-one