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Research on Chemical Intermediates

, Volume 45, Issue 3, pp 1583–1593 | Cite as

Cyclization of mercaptopyrimidine derivative: a facile synthetic approach for condensed pyrimidines

  • Maher FathallaEmail author
  • Weal Shehta
  • M. G. Assay
  • Eman Abd Alsalam
Article
  • 109 Downloads

Abstract

In the present study, we report the synthesis of different condensed pyrimidine derivatives by the exploitation of addition reactions to π-deficient systems or active methylene building blocks. For instance, the Diels–Alder reaction of pyrimidinethione 1 and benzalacetophenone 2 yielded pyridopyrimidine 5 (Scheme 1). On the other hand, the Michael addition of active methylene containing compounds to 1 produced derivatives 8, 10, 11, 12 and 14 (Scheme 2). The alkylation of 1 by ethylchloroacetate yielded 16. Furthermore, a triazinoquinazoline 19 was obtained through the cyclic condensation reaction of 1 with benzilmonohydrazone (Scheme 3). All reactions proceeded in good to moderate yields and the resulting compounds were characterized by different spectroscopic techniques.
Scheme 1

The synthesis of 5 by heterocyclization of pyrimidinethione 1 and benzalacetophenone 2

Scheme 2

Synthesis of quinazoline derivatives 8, 10, 11, 12 and 14

Keywords

Quinazoline Pyridopyrimidine Cycloaddition reactions Active methylene 

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceZagazig UniversityZagazigEgypt

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