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A New Family of Fused Azolo[1,5-a]pteridines and Azolo[5,1-b]purines.

ABSTRACT: 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 CS₂, glyoxal, triethyl orthoformate) with the formation of five- or six-membered annulated cycles.

SUBMITTER: Gazizov DA

PROVIDER: S-EPMC7391858 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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A New Family of Fused Azolo[1,5-a]pteridines and Azolo[5,1-b]purines.

Gazizov Denis A DA Gorbunov Evgeny B EB Rusinov Gennady L GL Ulomsky Evgeny N EN Charushin Valery N VN

ACS omega 20200714 29

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]pyrimid ...[more]

PMID: 32743198

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