Synthesis of 6-oxo-6,7,8,9-tetrahydro-10H-pyrimido-[5,4-b][1,4]benzoxazines and 6-oxo-6,7,8,9-tetrahydropyrimido[4,5-b][1,4]benzodioxanes |
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Authors: | N V Sazonov I E Mamaeva T S Safonova |
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Abstract: | Reaction of 5-hydroxy-6-aminopyrimidines with 2-bromohydroresorcinol and bromodimedone in DMF in the presence of sodium hydride
gave 6,7,8,9-tetrahydro-10H-pyrimido5,4-b]1,4]benzoxazines. When 4-chloro-5-hydroxy-6-aminopyrimidine was treated with bromodimedone
the principal products were 6,7,8,9-tetrahydropyrimido4,5-b]1,4]benzodioxanes. The nucleophilic substitution of the chlorine
atom in position 4 of the tetrahydropyrimidobenzoxazines by amines, sodium alkanoates, and thiourea has been studied and the
corresponding amines and alkoxy- and thio derivatives of this tricyclic system obtained.
Center for the Chemistry of Medicinal Substances, All Russian Chemico-Pharmaceutical Science Research Institute, Moscow 119815.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1411–1417, October, 1998. |
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