TY - JOUR
T1 - Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. IV
AU - Horiuchi, Jiroh
AU - Takeuchi, Yasuo
AU - Yamato, Masatoshi
PY - 1981
Y1 - 1981
N2 - 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.
AB - 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.
KW - 1,2,3,4-tetrahydroquinazolin-4-ones
KW - 1,4-dihydroquinolin-4-ones
KW - acetic anhydride
KW - acetylation
KW - rearrangement
UR - http://www.scopus.com/inward/record.url?scp=0019766822&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0019766822&partnerID=8YFLogxK
U2 - 10.1248/cpb.29.3130
DO - 10.1248/cpb.29.3130
M3 - Article
AN - SCOPUS:0019766822
SN - 0009-2363
VL - 29
SP - 3130
EP - 3133
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 11
ER -