Synthesis and properties of azoles and their derivatives. 35. Synthesis of certain azoles containing sterically hindered phenol residues

Келарев, В. И.; Shvekhgeimer, S. G.; Кошелев, В. Н.; Shvekhgeimer, G. A.; Lunin, A. F.

doi:10.1007/bf00506956

Chem Heterocycl Compd

1984

DOI: 10.1007/bf00506956

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Synthesis and properties of azoles and their derivatives. 35. Synthesis of certain azoles containing sterically hindered phenol residues

В. И. Келарев¹,

S. G. Shvekhgeimer²,

В. Н. Кошелев³

et al.

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Cited by 2 publications

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“…20 In the IR spectrum there are medium intensity bands at 1350-1330 and 1530-1520 cm À1 , corresponding to the C ¼ S bond vibrations, and there are no bands in the 2610-2530 cm À1 region characterizing the vibrations of the C-SH unit. 21 Thus, the spectral data suggest that compound 3 in the crystalline state, as well as in the DMSO solution, exists in a thionic form.…”

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Synthesis of Triazole Derivatives with Sterically Hindered Phenol Fragments

Кошелев

Primerova

Ivanova

et al. 2020

Organic Preparations and Procedures International

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In recent decades, the chemistry of functionally substituted 1,2,4-triazoles and the fused heterocyclic systems based on them have received significant attention due to their structural and biological characteristics. The 1,2,4-triazole ring is a fragment of many fungicides such as fluconazole, intraconazole, and voriconazole. 1 3-R-4-Amino-1,2,4-triazole-5-thiones were found to exhibit antimicrobial and anti-inflammatory activity. 2-5 Fused heterocyclic triazoles also possess important clinical applications; thus, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles were reported as antiviral, antifungal, and antitumor agents. 6-8 Anti-HIV activity was also found. 9 Sterically hindered phenols were reported to possess anti-inflammatory and antimicrobial properties, 10,11 in addition to their well-known antioxidant activity. 12 As a continuation of our studies on the synthesis of azoles containing a hindered phenol moiety, 13,14 in the present work we have synthesized a number of novel compounds: substituted arylideneamino-2,4-dihydro-3H-1,2,4-triazole-3-thiones, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 6-aryl/alkyl-amino[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazoles, based on 3-(4-hydroxy-2,6-di-tert-butylphenyl) propanoic acid hydrazide, in search of new structures potentially exhibiting useful properties. In this study two different approaches were used to prepare the starting 4-amino-3-[2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl]-1,2,4-triazole-5-thione 3 (Scheme 1). In the first case, 15,16 the reaction of the hydrazide 1 with carbon disulfide and methyl iodide took place in ethanol to give the methyl ester of dithiocarbazic acid 2 in two stages over 24 hours (see Experimental section). Heterocyclization of the compound 2 with hydrazine hydrate lead to the formation of 3-R-4-amino-1,2,4-triazol-5-thione 3 in 55% yield. In the second case the 1,2,4-triazole 3 was obtained by the interaction of equimolar amounts of 3-(4-hydroxy-3,5-di-tert-butylphenyl)propanoic acid 4 and thiocarbohydrazide. According to the published data, 17,18 this approach involves, in most cases, a short-term fusion of the initial reagents, but, in our case, even short heating of the reaction mixture above the melting point led to the destruction of the starting acid. So the reaction was carried out by refluxing

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confidence: 94%

Synthesis of Triazole Derivatives with Sterically Hindered Phenol Fragments

Кошелев

Primerova

Ivanova

et al. 2020

Organic Preparations and Procedures International

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“…4-(1H-Benzo[d]imidazol-2-yl)-2,6-di-tert-butylphenol can be obtained via two classical methods: (a) the Phillips-Ladenburg reaction (interaction of o-phenylenediamine with 3,5-di-tert-butyl-4-hydroxybenzylcarboxylic acid) [5] and (b) the Weidenhagen reaction (interaction of diaminobenzenes with 3,5-di-tert-butyl-4-hydroxybenzylaldehyde) [4,6]. Benzimidazole derivatives have been prepared via reaction of diaminobenzenes with 3,5-di-tert-butyl-4-hydroxybenzyl carboxyimidate hydrochloride [7,8]. An example of o-phenylenediamine reaction with S,Sethylenebisthio-2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone affording benzimidazole bearing a hindered phenol moiety has been described [9].…”

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confidence: 99%

Diphenyl[(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienylidene)-methyl]phosphonate in reactions with o-phenylenediamine

et al. 2015

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Synthesis and properties of azoles and their derivatives. 35. Synthesis of certain azoles containing sterically hindered phenol residues

Cited by 2 publications

References 5 publications

Synthesis of Triazole Derivatives with Sterically Hindered Phenol Fragments

Synthesis of Triazole Derivatives with Sterically Hindered Phenol Fragments

Diphenyl[(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienylidene)-methyl]phosphonate in reactions with o-phenylenediamine

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