Studies of Heterocyclic Compounds. II. Acetyl Transfer Reactions of 3-Acetoxy-1-acetyl-5-methylpyrazole and the Related Compounds

The individual reactions of acetyl group rearrangement are examined to elucidate the complicated formation of five acetylated products of 3-methylpyrazol-5-one (I). In heated acetic acid-anhydride mixture the initially formed 2-acetyl-3-hydroxy-5-methylpyrazole (II) reacts further to produce 1-acety...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 22; no. 1; pp. 214 - 223
Main Authors ARAKAWA, KIICHI, MIYASAKA, TADASHI, OCHI, HISAO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1974
Japan Science and Technology Agency
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Summary:The individual reactions of acetyl group rearrangement are examined to elucidate the complicated formation of five acetylated products of 3-methylpyrazol-5-one (I). In heated acetic acid-anhydride mixture the initially formed 2-acetyl-3-hydroxy-5-methylpyrazole (II) reacts further to produce 1-acetyl-3-hydroxy-5-methylpyrazole (III), 3-acetoxy-2-acetyl-5-methylpyrazole (IV) and finally 3-acetoxy-1-acetyl-5-methylpyrazole (V), while inter- as well as intra-molecular acetyl transfer reaction takes place. The diacetate (V) is a sort of activated ester and is proved to be effective as a mild acetylating reagent of primary and secondary amines.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.22.214