Synthesis of 6-oxo-6,7,8,9-tetrahydro-10H-pyrimido[5,4-<i>b</i>][1,4]benzoxazines and 6-oxo-6,7,8,9-tetrahydropyrimido[4,5-<i>b</i>][1,4]benzodioxanes

Authors

  • Н. B. Сазонов Center for the Chemistry of Medicinal Substances, All Russian Chemico-Pharmaceutical Science Research Institute, Moscow 119815
  • И. Е. Мамаева Center for the Chemistry of Medicinal Substances, All Russian Chemico-Pharmaceutical Science Research Institute, Moscow 119815
  • T. C. Сафонова Center for the Chemistry of Medicinal Substances, All Russian Chemico-Pharmaceutical Science Research Institute, Moscow 119815

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-pyrimido[5,4-b][1,4]benzoxazines. When 4-chloro-5-hydroxy-6-aminopyrimidine was treated with bromodimedone the principal products were 6,7,8,9-tetrahydropyrimido[4,5-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.

How to Cite
Sazonov, N. V.; Mamaeva, I. E.; Safonova, T. S. Chem. Heterocycl. Compd. 1998, 34, 1201. [Khim. Geterotsikl. Soedin. 1998, 34, 1411.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02319503

Downloads

Published

1998-10-25

Issue

No. 10 (1998)

Section

Original Papers