Polycyclic systems with the pyridopyrimidine and pteridine nuclei

I. V. Dyachenko, R. I. Vaskevich, M. V. Vovk

Abstract


The literary sources relating to the methods for obtaining polycyclic compounds with pyridopyrimidine and pteridine subunits have been systematized and analyzed. The synthetic potential of two main approaches to the processes of formation of these types of structures has been revealed: 1) annelation of the fused pyrimidine rings to the pyridine or diazine nuclei; 2) cyclization based on functional derivatives of fused pyrimidines. It has been shown that the core structures for implementation of the first approach are usually amino(iso)nicotinic acids, heteroaromatic halogen acids, isotiocyanatopyridine carboxylates, 1H-pyrido[2,3-d][1,3]oxazine-2,4-diones and 2-amino derivatives of pyridines or diazines. The convenient tools for formation of a fused pyrimidine ring such as the cross-coupling reaction by Buchwald-Hartwig through amination of haloarenes, the radical cascade cyclization of N-acylcyanamides and the intramolecular reaction of aza-Wittig have been described. The second approach focuses on the cycle formation processes involving hydrazinopyrimidines, 2-aminopyridopyrimidines and 2-thioxopyridopyrimidones. It has been noted that the electrophilic intramolecular cyclization under the action of halogenarylchalcogenides and mineral acids is an important factor for the directed synthesis of polycyclic systems based on alkenyl fused pyridopyrimidones or pteridones. In this review a considerable attention is paid to structures that exhibit pronounced biological effects.

Keywords


pyridopyrimidines; pteridines; polycyclic systems; intramolecular cyclization; annelation; biological activity

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DOI: https://doi.org/10.24959/ophcj.16.887

Abbreviated key title: Ž. org. farm. hìm.

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