Expedient synthesis of pyrazoles substituted with amino, hydroxyl and thioamide groups

Трофимов, Б. А.; Малькина, А. Г.; Borisova, Angela P.; Nosyreva, V. V.; Shemyakina, Olesya A.; Kazheva, Olga N.; Шилов, Г. В.; D’yachenko, O. A.

doi:10.1016/j.tetlet.2008.03.046

Cited by 16 publications

(11 citation statements)

References 30 publications

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“…16 The reaction of cyanoacetylenic alcohols 1 with thiosemicarbazide, under physiological conditions proceeded in chemo-, regio-and stereoselective fashion to produced trifunctionalized (amino, hydroxyl and thioamide functions) pyrazoles 22a-d in up to 91% yield (Scheme 17). 19 Scheme 17 The synthesis of pyrazoles 22 from cyanoacetylenic alcohols 1 and thiosemicarbazide 19 This cyclization is rather unexpected. Indeed, thiosemicarbazide usually attacks electron-deficient acetylenes (dimethyl acetylenedicarboxylate) by its sulfur atom.…”

Section: Methodsmentioning

confidence: 99%

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Трофимов¹,

Малькина²

2021

Synthesis

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Cyanoacetylenic alcohols, R1R2C(OH)C≡C-CN, the closest derivatives of cyanoacetylene, an interstellar abundant molecule, are now becoming acknowledgeable in modern organic synthesis which tends to mimic nature. Highly reactive C≡C and C≡N bonds in close vicinity of the hydroxyl group makes these molecules a chemical trinity of mutually influencing functions ensuring an endless number of chemical transformations. All reactions of cyanoacetylenic alcohols parallel modern organic synthesis, being biomimetic. They do not need transition metals (and in most cases, the metals at all except for physiologically indispensible Na+, K+), proceed at ambient temperature and often in aqueous media. Fundamentally, these reactions are 100% atom-economic because they are almost exclusively addition processes. Usually, in the cyanoacetylenic alcohols, cyano, acetylene and hydroxyl functions behave as inseparable entity providing the multiple functionalizations of the forming molecules. This allows hydroxyl, carbonyl, carboxylic, imino, amino, amido, cyanoamido, cyano, various P-containing, ether and ester functions, along with the double bonds and different fundamental heterocycles (furans, furanones, pyrazoles, oxazoles, pyridines, pyrimidines, purins, etc.) and diverse polycyclic systems to be integrated in a one molecular architecture. This review focuses on analysis and generalization of the knowledge accumulated in the chemistry of these cyanoacetylenic alcohols, mostly over the past 15 years.

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Section: Methodsmentioning

confidence: 99%

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Трофимов¹,

Малькина²

2021

Synthesis

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“…The hydrazones have been exhibited to have antibacterial [Singh et al, 1979;Mohammed et al, 1991;El-Ashry et al, 2003;Almeida et al, 2008;Contelles et al, 2008;Kumar et al, 2009;Sherman et al, 2008]. Anticonvulsant [Saeed et al, 2008;Trofimov et al, 2008;Xia et al, 2008;Zheng et al, 2009]. what's more, antitubercular activities [Trofimov et al, 2008;Xia et al, 2008;Zheng et al, 2009;Sriram et al, 2006;Abou-Melha et al, 2008;El-Tabl et al, 2008;A-Joshi et al, 2008].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of novel metal complexes containing hydrazone derived from camphor and 2,4-dinitrophenyl hydrazine

2019

University of Thi-Qar Journal of Science

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Ligand The development of 2,4-dinitrophenyl hydrazine with camphor under demonstrated conditions yielded another hydrazone ligand. The structures of metel (II) for example, copper, nickel, cobalt, zinc and iron with hydrazone have been composed from reacting between copper bromide, nickel chloride hexahydrate, cobalt chloride hexahydrate, zinc chloride, and iron bromide with hydrazone in 1:2 molar ratio. The ligand and their metal complexes have been detached in a solid state. The spectroscopic date of the structures proposes their 1:2 structures which are characterized by CHN, FT-IR and 1 H NMR spectroscopy. From spectroscopic reviews I proposed the octahedral structure for the all structures and the outcomes are spoken to and talked about underneath.

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“…Many studies describe the preparation of thioamide derivatives [1], [2], [5][6][7][8][9][10][11][12] , as the best known methods of adding isothiocyanates to secondary amines [1], or the thionation of amides [2], [4], [5] ; by the reaction of dialkylphosphite with isothiocyanate which gave reasonable yields of phosphothioamidates [11]- [12] . Furthermore They were a preparation of triethylphosphite-pyridinium iodide and isothiocyanates [13] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural Studies of phosphonothioamidates

Omrani

Amor

Bahri

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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The reaction of isothiocyanates with dialkylphosphites in the presence of strong base yielded the phosphonothioamides 2. Treatment of 2 with methyl iodide afforded the corresponding thioimidates 3 with high yields.All compounds were characterized on the basis of their IR, NMR Spectroscopy ( 1 H, 13 C, 19 F and 31 P) and in some cases by elemental analysis, HRMS data and calculations using Density Functional Theory (DFT)-B3LYP//6-311G** and evolution study by 31 P-NMR in an external lock with D2O. The conformational molecular structure of compounds 2d and 2f were determined by single-crystal X-ray diffraction analysis.

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Expedient synthesis of pyrazoles substituted with amino, hydroxyl and thioamide groups

Cited by 16 publications

References 30 publications

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Preparation and Characterization of novel metal complexes containing hydrazone derived from camphor and 2,4-dinitrophenyl hydrazine

Synthesis and structural Studies of phosphonothioamidates

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