Tautomerism and basicity of carboxylic acid guanyl hydrazides (acylaminoguanidines)

Aстахов, А. В.; Тарасова, Е. В.; Chernysheva, A. V.; Rybakov, Victor B.; Starikova, Z. A.; Чернышев, В. М.

doi:10.1007/s11172-021-3246-8

Cited by 3 publications

(2 citation statements)

References 92 publications

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“…Due to the fact that the guanyl hydrazide (5) formation step is acid-catalyzed and reversible, its success is highly dependent on the reaction conditions. In this regard, the following points are important: (i) reaction medium pH ≤ 1, (ii) to ensure rapid equilibrium attainment (it is necessary to use a concentrated solution with minimal water content), (iii) the application of an optimized excess of HCl acid as also shown previously [43,51].…”

Section: Resultsmentioning

confidence: 99%

“…Attempts to isolate and characterize aliphatic carboxylic acid guanyl hydrazides in the form of free bases proved unsuccessful. The treatment of salts with aqueous ammonia or sodium hydroxide succeeded by purification resulted in the cyclization of aliphatic carboxylic acid guanyl hydrazides to the corresponding aminotriazoles [43,51,52]. Thus, there are reasons to assume that the most difficult, and the rate determining stage in our process, is the acylation of guanidine to produce 5, which requires such a high temperature (180 • C), under which both stages with the elimination of water (2 to 5 and 5 to 7) can be effectively accomplished.…”

Section: Resultsmentioning

confidence: 99%

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Microwave-Assisted Synthesis of 5-Substituted 3-Amino-1,2,4-triazoles from Aminoguanidine Bicarbonate and Carboxylic Acids

Gümüş,

Gorobets,

Uludag

2024

Processes

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The effect of the molar ratio between reagents, reaction time and temperature on the yield of 5-substituted 3-amino-1,2,4-triazoles obtained by the direct condensation of carboxylic acids with aminoguanidine bicarbonate under acid catalysis conditions was studied. As a result, a general green straightforward synthesis of the title compounds bearing aliphatic substituents or a phenyl ring was developed using sealed reaction vials under controlled microwave synthesis conditions that are suitable for the application of volatile starting carboxylic acids. Our straightforward synthetic method proposed in this work increases the synthetic accessibility of these widely used building blocks and therefore is able to significantly expand the structural diversity of compounds containing a triazole moiety for the needs of drug discovery.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted Synthesis of 5-Substituted 3-Amino-1,2,4-triazoles from Aminoguanidine Bicarbonate and Carboxylic Acids

Gümüş,

Gorobets,

Uludag

2024

Processes

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Standard enthalpies of formation of para-substituted aromatic nitroso oxides

Khursan,

Safiullin

2023

Russ Chem Bull

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Unexpected Products of Salicylidene-Aminoguanidine Reactions with Metal Ions—Synthesis and Structural Aspects

Radanović,

Vojinović-Ješić,

Radulović

et al. 2024

Organics

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Due to the promising characteristics of aminoguanidine Schiff bases, ongoing research focuses on synthesizing and characterizing different compounds of this class to establish structure–property relationships. However, the pronounced alkalinity of the aminoguanidine residue makes isolating its Schiff bases in neutral form challenging. In the reaction of salicylidene-aminoguanidine ([HL]NO3) with a strong base (NaOH), the partially neutralized product of the formula [HL]NO3∙L·H2O was obtained in the form of single crystals. This compound could be considered a cocrystal in which protonated and neutral forms of the Schiff base coexist. Furthermore, the coordinating properties of [HL]NO3 towards zinc and organotin were investigated, and instead of the expected crystals of complex compounds, a novel polymorph of the ligand was obtained. Additionally, the reaction of [HL]NO3, NH4VO3 and salicylaldehyde was carried out to achieve the condensation of the free NH2-group in the aminoguanidinium fragment, targeting a vanadium(V) complex with tetradentate ligand. However, a purely organic compound containing three salicylaldehyde residues and two imine groups, i.e., C21H18N2O3, was isolated. All the obtained compounds were characterized by elemental and spectroscopic analysis, conductometry and SC-XRD analysis. The data were compared to those of similar structures, and the results provide further insight into the properties of these compounds and their future investigation for potential usage.

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Tautomerism and basicity of carboxylic acid guanyl hydrazides (acylaminoguanidines)

Cited by 3 publications

References 92 publications

Microwave-Assisted Synthesis of 5-Substituted 3-Amino-1,2,4-triazoles from Aminoguanidine Bicarbonate and Carboxylic Acids

Microwave-Assisted Synthesis of 5-Substituted 3-Amino-1,2,4-triazoles from Aminoguanidine Bicarbonate and Carboxylic Acids

Standard enthalpies of formation of para-substituted aromatic nitroso oxides

Unexpected Products of Salicylidene-Aminoguanidine Reactions with Metal Ions—Synthesis and Structural Aspects

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