Three-Component Reaction of Dimedone with Aromatic Aldehydes and 5-Aminotetrazole

Гейн, В. Л.; Prudnikova, A. N.; Kurbatova, A. A.; Дмитриев, М. В.; Новикова, В. В.; Рудакова, И. П.; Starikov, Andrey

doi:10.1134/s1070363219050049

Cited by 7 publications

(3 citation statements)

References 13 publications

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“…9-(2,5-Dimethoxyphenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1- b ]quinazolin-8(4 H )-one (where R = 2,5-(MeO) 2 C 6 H 3 ) shows significant analgesic activity and is better in activity to the comparison drug (metamizole sodium). 101…”

Section: Tetrazolopyrimidine Compoundsmentioning

confidence: 99%

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole

Javahershenas,

Makarem,

Mei

et al. 2024

Synthesis

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The unique reactivity and beneficial features of the 5-aminotetrazole synthon (1H-tetrazol-5-amine) have made it a versatile and effective building block in the synthesis of heterocyclic compounds. In addition, several drugs containing this scaffold with a wide array of biological properties have been already introduced. Heterocyclic structures are the backbone of many biologically active and industrially important compounds. 5-Aminotetrazole is one of the favored synthons used in the preparation of heterocycle-bearing compounds, especially in multicomponent synthesis. This review highlights a comprehensive overview of the emerging applications of 5-aminotetrazole as a key component in the synthesis of heterocyclic frameworks through multicomponent reactions, reported between 2017 and July 2023.1 Introduction2 5-Aminotetrazole3 Tetrazolopyrimidine Compounds4 Spiro Compounds5 Miscellaneous6 Conclusion

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Section: Tetrazolopyrimidine Compoundsmentioning

confidence: 99%

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole

Javahershenas,

Makarem,

Mei

et al. 2024

Synthesis

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“…Gein et al reported that reaction of dimedone with a mixture of 5-aminotetrazole monohydrate and substituted aromatic aldehyde taken in an equimolar ratio without solvent and catalyst at a temperature of 160–170 °C for 5–10 min afforded 9-aryl-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-ones 101 ( Figure 12 ) [ 106 ]. All compounds were found to have low antibacterial and antifungal activity (MIC > 1000 μg mL −1 ).…”

Section: Biginelli Reaction Mediated Synthesis Of Antimicrobial Pyrimidine Derivativesmentioning

confidence: 99%

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

Marinescu

2021

Molecules

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Antimicrobial resistance was one of the top priorities for global public health before the start of the 2019 coronavirus pandemic (COVID-19). Moreover, in this changing medical landscape due to COVID-19, finding new organic structures with antimicrobial and antiviral properties is a priority in current research. The Biginelli synthesis that mediates the production of pyrimidine compounds has been intensively studied in recent decades, especially due to the therapeutic properties of the resulting compounds, such as calcium channel blockers, anticancer, antiviral, antimicrobial, anti-inflammatory or antioxidant compounds. In this review we aim to review the Biginelli syntheses reported recently in the literature that mediates the synthesis of antimicrobial compounds, the spectrum of their medicinal properties, and the structure–activity relationship in the studied compounds.

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“…The products were isolated after 12–20 min in excellent yields. 74 To date, various practical approaches have been developed, wherein the same starting materials are being reacted in the presence of catalysts such as Fe 3 O 4 @chitosan, 75 Fe 3 O 4 @clay nanocomposite, 76 choline chloride:glycerol as a deep eutectic solvent, 77 1-methyl-1-sulfonic acid pyrrolidinium chloride [MPyrrSO 3 H]Cl/4-methyl-4-sulfonic acid morpholinium chloride [MMorSO 3 H]Cl, 78 Sc(OTf) 3 , 79 Brönsted acidic ionic liquid supported on rice husk ash (RHA-[pmim]HSO 4 ), 80 montmorillonite KSF as a heterogeneous catalyst, 81 nickel nanoparticles, 82 CAN, 83 microwave irradiation at 150 W, 84 hydrotalcite (Mg–Al–CO 3 ), 85 chitosan, 86 nanosheets AlPO 4 (SO 3 H), 87 graphene oxide (GO), 88 γ-Fe 2 O 3 @SiO 2 @[bis-APTES]Cl 2 nanoparticles, 89 and catalyst- and solvent-free conditions at 160–170 °C 90 by various research groups. All these methods were proven to be highly efficient, giving the products in excellent yields in a shorter time ( Scheme 24 ).…”

Section: Classificationmentioning

confidence: 99%

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

et al. 2021

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Three-Component Reaction of Dimedone with Aromatic Aldehydes and 5-Aminotetrazole

Cited by 7 publications

References 13 publications

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

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