Synthesis of 4-(hydroxyphenyl)-1,2,4-triazoles

Елохина, В. Н.; Нахманович, А. С.; Yaroshenko, T. I.; Stepanova, Z. V.; Ларина, Л. И.

doi:10.1134/s1070363206010312

Cited by 8 publications

(6 citation statements)

References 4 publications

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“…It was noticed that the yield of the 1,3-dithiin 211 during the reaction without the perchloric acid amounted to only 5%. On the whole it can be concluded that [5+1] cyclization of malonodithioamides in an acidic medium is realized with the participation of the S,S atoms (on account probably of the protonation of the N,N atoms) [100][101][102][103]105], whereas in a basic medium it takes place at the C, N and N,N atoms [97].…”

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 96%

“…It was shown [100][101][102][103] that the products from the reaction of malonodithioamides 204 with aroylacetylenes 205 in the presence of an equimolar amount of HClO 4 are 2-acylmethyl-4-amino-1,3-dithiin-6-R-iminium perchlorates 206. With the presence of triethylamine in the reaction solution cyclization of the acetylenes with malonodithioamides was not observed [104], and the only product was cis-(benzoylvinyl) disulfide 207.…”

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

“…A cycle of investigations of malonothioamides with acetylene derivatives was undertaken in [100][101][102][103][104][105]. It was shown [100][101][102][103] that the products from the reaction of malonodithioamides 204 with aroylacetylenes 205 in the presence of an equimolar amount of HClO 4 are 2-acylmethyl-4-amino-1,3-dithiin-6-R-iminium perchlorates 206.…”

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

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Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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Data from the last six years on the heterocyclization of thioamides containing an active methylene group are analyzed and classified.At the present time there has been a considerable increase in the number of publications on the chemistry of thioamides, and this is explained by the value of the compounds as initial reagents for further transformations and particularly for the synthesis of various sulfur-and nitrogen-containing heterocycles [1][2][3][4][5][6][7][8]. The enormous practical significant of the latter is common knowledge -they have found application as drugs, pesticides, dyes, and preservatives.Thioamides with an active methylene group are attractive synthesis units for the production of heterocycles. These polyfunctional compounds can be represented by the formula R 3 -CH 2 CS-NR 1 R 2 (where R 1 , R 2 = H, Alk, Ar; R 3 is an electron-withdrawing group such as CN, AlkCO, ArCO, (AlkO) 2 PO, AlkSO 2 , ArSO 2 , NO 2 ). The presence of another reaction center (the methylene group) makes it possible to use them as N-С-С and S-C-C components for various condensations [1][2][3][4][5][6][7][8]. A special feature of such substrates is the ability to react both with dinucleophilic and with dielectrophilic and dipolar reagents. As a rule the products of these heterocyclizations contain functional groups, which makes it possible to achieve their modification or annelation. Such characteristics of thioamides with an active methylene group substantially increase their synthetic potential and extend the range of accessible heterosystems, while the use of modern physical methods of investigation (X-ray crystallographic analysis and 1D and 2D NMR spectroscopy) makes it possible to establish the structure of the obtained compounds unambiguously. The presence of biological activity in the products of these transformations also attracts investigators to this subject [5][6][7][8].The reason for the appearance of this review was the increasing need for generalization and classification of new information on the heterocyclization of such thioamides that had not been included in previous reviews [2][3][4][5] and also to define the trends in the study of these processes. Since one of the most important reports in this field is the review [1] we undertook an analysis of the literature that has appeared in the last six years.

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Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 96%

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

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Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…The maximal electroshock (MES) test showed that this type of synthetic compounds exhibited strong potency at a dose of 30 mg/kg against MES induced seizure in mice and also possessed remarkable lower neurotoxicity [104]. By the similar procedure, triazole fragment was coupled with 2-substituted benzooxazole to give molecules with broad bioactive spectrum [105] and other 4-(hydroxyphenyl)-1,2,4-triazole derivatives were also able to be prepared efficiently [106].…”

Section: Alkyl Hydrazidesmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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“…Two complexes of copper chloride with 4 (4 hydroxyphenyl) 1,2,4 triazole of the formulas [Cu 6 (μ 6 Cl)(μ 3 OH) 2 (μ L) 6 [11]. The hexanuclear complex [Cu 6 (μ 6 Cl)(μ 3 OH) 2 (μ L) 6 [12]. ).…”

mentioning

confidence: 98%

Synthesis and study of cobalt(II), nickel(II), and copper(II) complexes with 4-(4-hydroxyphenyl)-1,2,4-triazole

et al. 2012

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The syntheses and physicochemical studies of tran sition metal complexes with 1,2,4 triazoles constantly attract the attention of researchers [1]. This attention is due to wide practical applications of 1,2,4 triazole and its derivatives as biologically active compounds, analytical and photosensitive reagents, etc.From the viewpoint of the development of coordi nation chemistry, 1,2,4 triazoles are promising ligands under active study because of various structures and properties of their metal complexes. Unsubstituted 1,2,4 triazole and its 3,4,5 substituted derivatives containing no coordinating substituents usually show bidentate bridging coordination giving rise to di , tri, and polynuclear complexes [1,2]. Polynuclear com plexes can have chain [1], layered [3], or framework structures [4]. The presence of a bulky substituent in the side chain of 1,2,4 triazole is unfavorable for the growth of a polymer chain, so complexation mainly yields dinuclear [5] or trinuclear complexes [6][7][8][9].The goal of this study was to obtain and examine cobalt(II), nickel(II), and copper(II) complexes with 4 (4 hydroxyphenyl) 1,2,4 triazole (L). Complex ation reactions with 4 (hydroxyphenyl) 1,2,4 triaz oles is poorly studied. For instance, the synthesis of complexes from Mn(II), Ni(II), and Zn(II) tetrafluo roborates, Cd(II) perchlorate, and 4 (3 hydroxyphe nyl) 1,2,4 triazole (L 1 ) has been reported in [9]. Ear lier, we have obtained and described a number of tri nuclear Co(II), Ni(II), and Cu(II) complexes with the same ligand of the formulas [Co 3 (L 1 ) 6 (H 2 O) 5 . In all the complexes, the cation [M 3 (L 1 ) 6 (H 2 O) 6 ] 6+ has a trinu clear structure. Two complexes of copper chloride with 4 (4 hydroxyphenyl) 1,2,4 triazole of the formulas [Cu 6 (μ 6 Cl)(μ 3 OH) 2 (μ L) 6 Cl 9 (H 2 O) 3 ] ⋅ 3H 2 O and {[Cu(μ L)(μ OH)(H 2 O) 2 ]Cl} ∞ have been described in [11]. The hexanuclear complex [Cu 6 (μ 6 Cl)(μ 3 OH) 2 (μ L) 6 Cl 9 (H 2 O) 3 ] ⋅ 3H 2 O has an unusual struc ture. Three molecules of L are coordinated to the cop per(II) ions in a bidentate bridging fashion to form two triangles linked by the ligand μ 6 Cl. The complex {[Cu(μ L)(μ OH)(H 2 O) 2 ]Cl} ∞ contains both the bridging molecule of L and the bridging hydroxy group.We found it expedient to extend the range of com plexes with 4 (4 hydroxyphenyl) 1,2,4 triazole and study the influence of the metal and anion nature on the compositions and structures of the complexes. EXPERIMENTALThe salts Co(NO 3 ) 2 ⋅ 6H 2 O, Ni(NO 3 ) 2 ⋅ 6H 2 O, Co(ClO 4 ) 2 ⋅ 6H 2 O, NiCl 2 ⋅ 6H 2 O, Ni(ClO 4 ) 2 ⋅ 6H 2 O, and Cu(ClO 4 ) 2 ⋅ 6H 2 O (high purity grade) were used without further purification. 4 (4 Hydroxyphenyl) 1,2,4 triazole (Т m = 285-286°С) was prepared as described in [12].Abstract-New complexes of Co(II), Ni(II), and Cu(II) nitrates, chlorides, and perchlorates with 4 (4 hydroxyphenyl) 1,2,4 triazole (L) were obtained and examined by single crystal X ray diffraction, X ray powder diffraction, and electronic absorption and IR spectroscopy. The cations of all the complex...

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Synthesis of 4-(hydroxyphenyl)-1,2,4-triazoles

Cited by 8 publications

References 4 publications

Heterocyclization of thioamides containing an active methylene group (review)

Heterocyclization of thioamides containing an active methylene group (review)

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Synthesis and study of cobalt(II), nickel(II), and copper(II) complexes with 4-(4-hydroxyphenyl)-1,2,4-triazole

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