The reaction of 2-substituted 1-methyl-1,2,3,4-tetrahydroquinazolin-4-ones (THQ) with acetic anhydride afforded two types of products depending on the number of C2-substituents. The reaction of 2-monosubstituted 1-methyl-THQ (6) gave the corresponding N3-acetyl-THQ derivatives (7), while the reaction of 2,2-disubstituted 1-methyl-THQ (8) afforded rearranged products, 2,3-disubstituted 1-methyl-1,4-dihydroquinolin-4-ones (9). A mechanism is proposed for the reaction of 8 to give 9.
|Number of pages||4|
|Journal||Chemical and Pharmaceutical Bulletin|
|Publication status||Published - 1981|
- acetic anhydride
ASJC Scopus subject areas
- Drug Discovery