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Search for "3-amino-1,2,4-triazole" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.
Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines
Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27
- Republic 10.3762/bjoc.16.27 Abstract Four-component reactions of 3-amino-1,2,4-triazole or 5-amino-1H-pyrazole-4-carbonitrile with aromatic aldehydes and pyruvic acid or its esters under ultrasonication were studied. Unusual for such a reaction type, a cascade of elementary stages led to the formation of
- 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines. Keywords: 5-amino-1H-pyrazole-4-carbonitrile; 3-amino-1,2,4-triazole; 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines; heterocycle; multicomponent reaction; ultrasonication; Introduction Tetrahydropyrimidines are heterocycles of high pharmacological
- . Therefore, the present work is devoted to the study of multicomponent reactions involving 3-amino-1,2,4-triazole or 5-aminopyrazoles, aromatic aldehydes, and pyruvic acid or its esters under ultrasonication. Results and Discussion It was discovered that MCRs involving 3-amino-1,2,4-triazole or 5-amino-1H
In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231
- accessible by variation of the binucleophilic component 1 (instead of 1, 3-amino-1,2,4-triazole, 2-aminobenzimidazole, 3-aminopyrazoles, 4-amino-1,2,3-triazoles, etc. can be used [13]). However, a relatively low reactivity of amine 1 due to the electron deficiency of the tetrazole ring has been reported
15N-Labelling and structure determination of adamantylated azolo-azines in solution
Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250
- by the reisomerization of the initially formed N2-adamantylated product (15a-15N2). Indeed, 2 h of refluxing of isolated 15a-15N2 in TFA with 1.5 molar equivalents of 14 yielded a mixture of compounds 15a-15N2 and 15b-15N2 in the same (1:2) ratio (Scheme 1). The use of [1-15N]-3-amino-1,2,4-triazole
- -amino-1,2,4-triazole 16-15N2 was synthesized by the interaction of 15N2-hydrazine sulphate (98%, 15N) with S-methyl isothiourea sulphate and consecutive cyclization with formic acid (see the Supporting Information File 1). The use of 16-15N2 in a reaction with ethyl 4,4,4-trifluoroacetoacetate (22
- -15N2 (Scheme 2). However, prolonged (6 h) refluxing of the N3-regioisomer with 1.5 molar equivalents of 1-adamantanol (14) in a TFA solution led to complete isomerization of the compound and re-attachment of adamantane to the N4-atom of the azine ring (compound 21b-15N2). Double-labelled [1,2-15N2]-3
New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104
- sometimes similar to 3-amino-1,2,4-triazole that was described as a component of GBB-3CR earlier [71][72][73][74][75]. Therefore, the first type of aminoazoles studied in our work was 5-amino-N-aryl-1H-pyrazole-4-carboxamide that showed 1,3-binucleophile properties in the condensation with aromatic
The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles
Beilstein J. Org. Chem. 2015, 11, 385–391, doi:10.3762/bjoc.11.44
- preparation of compound 11 in the reaction of ester 1f with 5-AT was unexpected, because it is known that ester 1f interacts with 3-amino-1,2,4-triazole in refluxing ethanol [8] and with substituted 5-amino-1,2,4-triazoles in acetic acid [34] to afford triazolo[1,5-a]pyrimidines. However, we did not observe
The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320
- derivatives from salicylaldehyde, various dicarbonyl compounds, and urea (thiourea) using PdO as a catalyst (Scheme 2). Heterocyclizations involving both, salicylaldehyde and aminoazoles, are intriguing as well. Thus, for example in the course of the study on the application of 3-amino-1,2,4-triazole and
Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236
- mixture even in trace amounts by TLC, while aminotriazole 1 was isolated unchanged from the reaction mixture. Positional-isomeric compounds 3, whose formation had been expected according to the data published earlier for the similar reactions of 3-amino-1,2,4-triazole [29], was not isolated or even
- boiling dry ethanol or under MW heating in methanol. The same procedure also allowed us to obtain compounds 5a,b. The best results in this case were observed when the microwave-assisted procedure (Method D) was applied. It should be noted that for similar treatments involving 3-amino-1,2,4-triazole [7][29
Advances in synthetic approach to and antifungal activity of triazoles
Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79
- different substituents to the triazole nucleus. By a judicious choice of ligands, a library of new luminescent ionic iridium complexes was prepared [71]. 3-Amino-1,2,4-triazole is an inhibitor of mitochondrial and chloroplast function. Commercial grade 3-amino-1,2,4-triazole is used as a herbicide and
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