A New Family of Fused Azolo[1,5- a ]pteridines and Azolo[5,1- b ]purines.
| Autor: | Gazizov DA; Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, Sofia Kovalevskoy St. 22/20, Ekaterinburg 620108, Russia., Gorbunov EB; Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, Sofia Kovalevskoy St. 22/20, Ekaterinburg 620108, Russia., Rusinov GL; Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, Sofia Kovalevskoy St. 22/20, Ekaterinburg 620108, Russia.; Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia., Ulomsky EN; Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, Sofia Kovalevskoy St. 22/20, Ekaterinburg 620108, Russia.; Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia., Charushin VN; Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, Sofia Kovalevskoy St. 22/20, Ekaterinburg 620108, Russia.; Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia. |
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| Jazyk: | angličtina |
| Zdroj: | ACS omega [ACS Omega] 2020 Jul 14; Vol. 5 (29), pp. 18226-18233. Date of Electronic Publication: 2020 Jul 14 (Print Publication: 2020). |
| DOI: | 10.1021/acsomega.0c01849 |
| Abstrakt: | The nitration of azolo[1,5- a ]pyrimidin-7-amines with several nitration agents (such as acetic nitric anhydride, nitronium tetrafluoroborate, and a mixture of concentrated nitric acid and sulfuric acid) has been investigated. It has been shown that, depending on the conditions, the nitration of pyrazolopyrimidin-7-amines bearing electron-withdrawing groups in the pyrazole ring leads to nitration products in the pyrimidine and/or pyrazole ring. The nitration of triazolo[1,5- a ]pyrimidin-7-amines with "nitrating mixture" has been optimized, thus allowing us to obtain a series of 6-nitro[1,2,4]triazolo[1,5- a ]pyrimidin-7-amines, followed by their reduction into the corresponding [1,2,4]triazolo[1,5- a ]pyrimidin-6,7-diamines (yields 86-89%). The latter have been subjected to heterocyclization by a variety of electrophilic compounds (such as CS Competing Interests: The authors declare no competing financial interest. (Copyright © 2020 American Chemical Society.) |
| Databáze: | MEDLINE |
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