T. Kinoshita, Y. Takaishi, T. Okunaka
Jul 1, 1992
Citations
0
Influential Citations
6
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The reactions of 1-(bromoalkyl)-5-bromo-6-bromomethyl-3-methyl-2,4(1H,3H)-pyrimidinedione (1) with several nucleophiles were examined as follows: by reaction with sodium methoxide, 6-(bismethoxy)methyl-5-debrominated derivatives 2, 3, and 4 were prepared; the corresponding di-substituted compounds (side chains in 1-and 6-positions) 5, 6, 7, and 9 were obtained by treatment with silver nitrate, silver acetate, potassium thiocyanate, and potassium thioacetate; the reaction with thioacetamide and iso-butylamine gave bicyclic compounds [1,4]thiazino[4,3-c]- 11, pyrazino[1,2-c]- 12, and [1,4]diazepino[1,2-c]pyrimidinedione 13, respectively; pyrrolidine, morpholine, and sodium azide afforded the corresponding 6-substituted compounds 14, 15, and 16.