Abstract
2-Thioxopyrimidinyl-5-(N,N-dimethylamino)formamidine (5) and 1,3-diphenyltriazolo[3,4-d]pyrimidinyl-N,N-dimethylformamidine (14) were prepared by condensation of 6-amino-2-thioxo-1,3-dihydropyrimidin-4-one (2) and 7-amino-1,3-diphenyl-1,2,4-triazolo[4,3-a]pyrimidin-4-one (13) with dimethylformamide dimethyl- acetal (DMFDMA). Compound 5 reacts with acetophenone and 2-acetylthiophene to give the 2-thioxo-1,3-dihydropyridino[2,3-d]pyrimidin-4-ones 3a and 3b, respectively. Compounds 3a,b react with hydrazonoyl halides 6,7 to give pyridino[2,3-d]triazolo[4,5-a]pyrimidin-4-ones 11a-d and not the isomeric structures 12a-d. Formamidines of type 14 react with ethyl cyanoacetate, malononitrile and benzoyl acetonitrile to give the 1,3-diphenyl-3a-hydropyridino[2,3-d]1,2,4-triazolo[4,5-a]pyrimidin-4-one derivatives 15a,b and 18, respectively. The structures of the newly synthesized compounds are established on the basis of chemical and spectroscopic evidences as well as their synthesis by alternative methods.
Highlights
Azoloazine derivatives form a very interesting class of compounds because of their significant biological and pharmaceutical activities and their chemistry is receiving considerable attention [1,2,3,4]
We wish to report the reaction of pyridino[2,3-d]pyrimidines 3 with hydrazonoyl halides 6,7 to give novel functionalized heterocycles having pyridine rings condensed with other important heterocycles such as pyrimidines and triazolopyrimidines
We report the synthesis of heterocyclic compounds 3, 5, 11, 14, 15 and 18 and the confirmation of the structures of the resulting products by spectroscopic data as well as their synthesis by alternative methods
Summary
Azoloazine derivatives form a very interesting class of compounds because of their significant biological and pharmaceutical activities and their chemistry is receiving considerable attention [1,2,3,4]. The exact structure of the reaction products could not be established unequivocally, because several close similar isomeric products could conceivably be formed. We report the synthesis of heterocyclic compounds 3, 5, 11, 14, 15 and 18 and the confirmation of the structures of the resulting products by spectroscopic data as well as their synthesis by alternative methods. The newly synthesized compounds appear to be promising substrates for further chemical transformations as well as biological activity evaluations
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