Journal of Organic Chemistry p. 5127 - 5132 (1985)
Update date:2022-07-30
Topics:
Boyle, Peter H.
Lockhart, Ronan J.
Reaction of 5-amino-7-(methylthio)furazano<3,4-d>pyrimidine (4) with a range of alcohols in the presence of bromine leads to the formation of the corresponding 5-amino-7-alkoxyfurazano<3,4-d>pyrimidines (5-10).These on hydrogenolysis afford 6-alkoxy-2,4,5-triaminopyrimidines, which can be condensed with benzil to give 2-amino-4-alkoxypteridines (17-21).The product from hydrogenolysis of 5-amino-7-(2-chloroethoxy)furazano<3,4-d>pyrimidine (7), however, undergoes intramolecular cyclization to a 2,3-dihydrooxazolo<3,2-c>pyrimidinium compound (23), which behaves as a heteronuclear resonance stabilized ambident cation.Reaction of it with nucleophiles followed by condensation with benzil leads to N3-substituted pteridines.
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Doi:10.1016/0022-1139(96)03444-6
(1996)Doi:10.1021/jacs.1c06228
(2021)Doi:10.1021/jo01118a009
(1956)Doi:10.1007/BF00956082
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(2019)Doi:10.1007/BF00504400
(1985)