A synthesis of 6-functionalized 7-unsubstituted- and 7-methyl[1,2,4]azolo[1,5-<i>a</i>]pyrimidine derivatives

Колосов, Максим А.; Shvets, Elena H.; Manuenkov, Dmitriy A.; Кулык, Олеся Г.; Orlov, V. D.

doi:10.1080/00397911.2019.1566476

Cited by 4 publications

(2 citation statements)

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“…Alkylation by methyl iodide, dimethyl sulfate, benzyl chloride/bromide, ethyl bromide/iodide, phenacyl bromide, ethyl chloroacetate, α‐chloroacetamide, α‐chloroacetonitrile occurs at the N atom of the dihydropyrimidine ring (reaction e , Scheme 6) [35,38–46] (sometimes together with the N‐alkylation of the azole ring [41,43,47] ). Arylation of dihydroazolopyrimidines by 3‐(trifluoromethyl)phenylboronic acid (Chan‐Lam coupling) leads to N‐aryl substituted derivatives (reaction f ) [48,49] .…”

Section: General Features and Historymentioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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Dihydroazolopyrimidines are an important class of heterocycles that are isosteric to natural purines and are therefore of great interest primarily as drug‐like molecules. In contrast to the heteroaromatic analogs, synthetic approaches to these compounds were developed much later, and their chemical properties and biological activity have not been studied in detail until recently. In the review, different ways to build dihydroazolopyrimidine systems from different building blocks are described – via the initial formation of a partially hydrogenated pyrimidine ring or an azole ring, as well as a one‐pot assembly of azole and azine fragments. Special attention is given to modern approaches: multicomponent reactions, green chemistry, and the use of non‐classical activation methods. Information on the chemical properties of dihydroazolopyrimidines and the prospects for their use in the design of drugs of various profiles are also summarized in this review.

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Section: General Features and Historymentioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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“…Generally, all three approaches allow for the preparation of a broad range of compounds 3 with a wide variety of substituents R 1 –R 3 . However, the vast majority of reported data [5–12 14–18] comprises aryl-substituted azolopyrimidines (with either R 1 or R 3 or both being aromatic substituents), and there are only a view examples of compounds 3 having no aryl substituent [19–20]. The reason for this relatively low synthetic availability might be due to their higher solubility (compared to aryl-substituted analogues) and difficulties associated with their isolation.…”

Section: Introductionmentioning

confidence: 99%

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Tkachenko

Komykhov

Мусатов

et al. 2019

Beilstein J. Org. Chem.

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The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.

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Five-membered ring systems: with more than one N atom

Yet

2021

Progress in Heterocyclic Chemistry

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A synthesis of 6-functionalized 7-unsubstituted- and 7-methyl[1,2,4]azolo[1,5-a]pyrimidine derivatives

Cited by 4 publications

References 10 publications

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Five-membered ring systems: with more than one N atom

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