Novel variants of the multicomponent reaction for the synthesis of 1,2,4-triazolo[1,5-а]pyrimidines and pyrido[3,4-е][1,2,4]triazolo[1,5-а]pyrimidines

Polikarchuk, V. A.; Chertova, Yuliya V.; Potapov, A. Yu.; Ledenyova, Irina V.; Kosheleva, Yevgeniya A.; Krysin, M. Yu.; Kozadyorov, Oleg А.; Shatalov, G. V.; Vandyshev, Dmitriy Yu.; Shikhaliev, Kh. S.; Chetti, Prabhakar

doi:10.1007/s10593-020-02773-7

Cited by 3 publications

(2 citation statements)

References 35 publications

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“…The method for the synthesis of podands containing a 4,7-dihydro-[1,2,4]-triazolo[1,5-a]pyrimidine moiety 134 (10-37 %) involving the Biginelli reaction of polyethers containing 3-oxobutanoyl, benzaldehyde or thiophene-2-carbaldehyde, and 3-amino-1,2,4-triazole moieties in the presence of CF 3 CO 2 H as a catalyst in THF as a solvent (Scheme 89) was reported by Filatova et al [99] Polikarchuk et al [100] developed a novel one-pot route towards synthesizing functional 1,2,4-triazolo[1,5-a]pyrimidines 135 (41-58 %) by way of a multicomponent regioselective reaction of aminotriazoles, β-ketoglutaric acid dimethyl diester, and dimethylformamide dimethyl acetal in refluxing acetonitrile (Scheme 90) according to the general mechanism described for this type of condensation.…”

Section: Chemistryselectmentioning

confidence: 93%

“…Polikarchuk et al [100] . developed a novel one‐pot route towards synthesizing functional 1,2,4‐triazolo[1,5‐ a ]pyrimidines 135 (41–58 %) by way of a multicomponent regioselective reaction of aminotriazoles, β‐ketoglutaric acid dimethyl diester, and dimethylformamide dimethyl acetal in refluxing acetonitrile (Scheme 90) according to the general mechanism described for this type of condensation.…”

Section: Triazolopyrimidine Synthesismentioning

confidence: 99%

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Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

et al. 2023

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One or more nitrogen‐containing molecules constitute an important class of heterocyclic compounds in organic synthesis, due to their reactivity and their presence in many molecules of natural, human or plant origin. These nitrogenous heterocycles play an essential role in various scientific domains, whether they are chemical, biological or pharmacological. N‐heterocycles are the privileged source of many research topics developed by several groups of researchers. Thus, different methods have been developed to access these heterocyclic compounds with nitrogenous rings, such as triazolopyrimidines. In this review, a bibliographic study summarizing the pharmacological importance of the triazolo[1,5‐a]pyrimidine ring, the different synthesis routes of these derivatives as well as their reactivity was reported.

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Section: Chemistryselectmentioning

confidence: 93%

Section: Triazolopyrimidine Synthesismentioning

confidence: 99%

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

et al. 2023

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Estimation of multicomponent reactions’ yields from networks of mechanistic steps

Szymkuć,

Wołos,

Roszak

et al. 2024

Nat Commun

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This work describes estimation of yields of complex, multicomponent reactions (MCRs) based on the modeled networks of mechanistic steps spanning both the main reaction pathway as well as immediate and downstream side reactions. Because experimental values of the kinetic rate constants for individual mechanistic transforms are extremely sparse, these constants are approximated here using Mayr’s nucleophilicity and electrophilicity parameters fine-tuned by correction terms grounded in linear free-energy relationships. With this formalism, the model trained on the mechanistic networks of only 20 – but mechanistically- and yield-diverse MCRs – transfers well to newly discovered MCRs that are based on markedly different mechanisms and types of individual mechanistic transforms. These results suggest that mechanistic-level approach to yield estimation may be a useful alternative to models that are derived from full-reaction data and lack information about yield-lowering side reactions.

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Advancements in the Synthesis of Triazolopyrimidines

Singh,

Lakhia,

Yadav

et al. 2024

COC

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The triazolopyrimidine scaffold indeed holds a prominent place in medicinal chemistry due to its versatile pharmacological properties. Researchers have explored the scaffold and its derivatives for various therapeutic applications. The unique structure of triazolopyrimidine has made it a valuable template for designing medicinally active molecules. The literature is full of studies showcasing the synthesis and biological activities of compounds containing the triazolopyrimidine ring, either fused or coupled with other heterocycles. The aim of this review is to provide a comprehensive and general summary of the recent advancements in the synthesis of triazolopyrimidine derivatives (Year 2021 to present).

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Novel variants of the multicomponent reaction for the synthesis of 1,2,4-triazolo[1,5-а]pyrimidines and pyrido[3,4-е][1,2,4]triazolo[1,5-а]pyrimidines

Cited by 3 publications

References 35 publications

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

Estimation of multicomponent reactions’ yields from networks of mechanistic steps

Advancements in the Synthesis of Triazolopyrimidines

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