Journal of the Chemical Society. Perkin transactions I p. 725 - 732 (1988)
Update date:2022-07-30
Topics:
Yamamoto, Yohsuke
Sakaguchi, Akira
Yoshida, Hiroshi
Akiba, Kin-ya
Reactions of N-silyl- or N-acyl-pyrimidinium salts with enol trimethylsilyl ethers were carried out to afford the adducts with a 2-oxoalkyl group, that is, 2-hydroxy-4-(2-oxoalkyl)-1,2,3,4-tetrahydro-pyrimidines (9) or the 3-acyl derivatives (8), respectively.Monoacylation of compounds (9) gave monoamides (8) in high yields.Exhaustive acylation of diamines (9) with a large excess of 2,2,2-trichloroethyl chloroformate in the presence of pyridine gave bicyclic compounds, 2-oxa-8,9-diazabicyclo<3.3.1>nona-3,6-dienes (14).By addition of trifluoroacetic acid, compounds (14) were reopened to afford 3,4-dihydropyrimidinium salts (11'), which were subjected to nucleophilic attack to give 1,2,3,4-tetrahydopyrimidines (16) in high yield.
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(1988)
