2-PHENYL-2,1,3-TRIAZOLE-4-CARBOXALDEHYDE AND DERIVATIVES<sup>1</sup>

Riebsomer, J. L.; Sumrell, Gene

doi:10.1021/jo01164a004

Cited by 21 publications

(12 citation statements)

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“…X-ray crystal structure was obtained using R-AXIS SPIDER X-ray diffraction. The synthesis of 1-phenyl-3-methyl-5-aryloxyl-pyrazol-4-methylene-para-substitutedacetiphenones(2a-e) [20]. Acetophenone 1a-e (20 mmoles) was added to a solution of 1-phenyl-3-methyl-5-aryloxyl-pyrazol-4-carboxaldehyde (20 mmoles) in aqueous KOH (10 mL, 35 % KOH) at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Xie

Liu

et al. 2008

Journal of Heterocyclic Chem

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A series of 1-acetyl(or phenyl)-3-aryl-5-(1-phenyl-3-methyl-5-aryloxyl-pyrazol)-4,5-dihydropyrazole derivatives have been efficiently synthesized under refluxing in glacial acetic acid with two kinds of hydrazines and five kinds of chalcones of 1-phenyl-methyl-5-phenoxyl-pyrazol-4-aldehyde. The structures were confirmed on the basis of 1 H NMR, IR, MS and element analysis, and the crystal structure of the compound 4c was determined by single crystal X-ray diffraction. The compound 4c belongs to monoclinic system with space group P2(1)/n, a = 11.8779(3) nm, b = 12.0901(2) nm, c = 17.7004(4) nm, = 90°, = 100.05(10)°, = 90°, Formula weight: 549.46, Triclinic V =2502.89(9) nm 3 , D c =1.458 Mg/m 3 , Z = 4, F (000) = 1128.

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Section: Methodsmentioning

confidence: 99%

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Xie

Liu

et al. 2008

Journal of Heterocyclic Chem

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“…El Khadem e colaboradores 18 prepararam dezenas de triazóis por este método, para posterior utilização na obtenção de corantes para celulose e na preparação de derivados da sulfa. Posteriormente, Riebsomer e Sumrell 19 ampliaram a abrangência desta reação, clivando a parte glicídica, levando à produção dos triazóis 23 ou 24 (Esquema 2). El Khadem 20 , estudando o mecanismo desta reação, mostrou que as osazonas formam um complexo osazona-Cu(II) o qual, quando submetido à oxidação e redução, fornece como produtos anilina, cobre metáli-co e osotriazol 22.…”

Section: Metodologia Via Osazonaunclassified

Heterociclos 1,2,3-triazólicos: histórico, métodos de preparação, aplicações e atividades farmacológicas

Melo¹,

Donnici²,

Augusti³

et al. 2006

Quím. Nova

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Recebido em 7/4/05; aceito em 21/7/05; publicado na web em 16/2/06 1,2,3-TRIAZOLIC HETEROCYCLES: HISTORY, PREPARATIONS, APPLICATIONS AND PHARMACOLOGICAL ACTIVITIES. The 1,2,3-triazole, known since the end of 19 th century, is a very widely used heterocyclic system present in many synthetic substances and commercial pharmaceutical compounds. In fact, 1,2,3-triazoles show several applications in many areas especially as medicines against many diseases like cancer, AIDS, Parkinson and Alzheimer. Nowadays there is a large variety of known methods to obtain these heterocyclic compounds comprising mainly three synthetic routes. Nevertheless, there is no article that gives an objective overview of the synthetic methods for obtaining these kinds of azoheterocycles. This paper presents a brief history of this class of compounds, and a synthetic discussion concerning the main synthetic methods for its preparation, such as cyclization through hydrazones, concerted cycloadditon [2+3] and pseudopericyclic cyclization -and some others of restricted application, but also important. Finally, this paper also provides a brief overview on pharmacological applications of some 1,2,3-triazoles.

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“…1-Benzyl-1,2,3-triazole-4,5-dicarboxylic acid [5], 1-butyl-1,2,3-triazole-4,5-dicarboxylic acid [5], 3-azido-1,2,4-triazole [6], 4-carboxy-5-methyl-2-phenyl-1,2,3-triazole [7], 4-carboxy-5-methyl-1-phenyl-1,2,3-triazole [8], 5-ethoxycarbonyl-4-methyl-2-phenyl-1,2,3-triazole-1-oxide [9], diphenylphosphoryl azide [10], 5-azidomethyltetrazole [11], 4,5-(dihydroxymethyl)furazan [12], 2-phenyl-1,2,3-triazole-4-carboxylic acid [13], 1-benzyl-4,5-(dihydroxymethyl)-1,2,3-triazole [14], and 1-benzyl-4-hydroxymethyl-1,2,3-triazole [14] were prepared by the known method.…”

Section: Methodsmentioning

confidence: 99%

The curtius reaction in the synthesis of noncondensed polynuclear azoles

Vereshchagin

Golobokova

Pokatilov

et al. 2011

Chem Heterocycl Comp

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Polynuclear noncondensed systems in which the azole rings are bound by urethane or carbamide fragments have been synthesized by the reaction of azole carboxylic acid azides with heterocyclic alcohols.With the aim to synthesize noncondensed polynuclear azole containing systems we have previously [1, 2] used methods of adding heterocycles to the core structure having an active substituent in the form of an azide, nitrile, or chloromethyl group, halogen, or acetylenic bond. The methods allow us to connect a number of heterocycles separated by a methylene group or by other fragments.In this study continuing our work on the synthesis of polynuclear heterocyclic structures we have examined the possible use of the Curtius rearrangement of heterocyclic acid azides to isocyanates and their subsequent reaction with azole-containing alcohols to yield polynuclear structures in which the azole rings are separated by carbamide or urethane fragments.It is known that acyl and aroyl azides undergo the Curtius rearrangement upon heating to give alkyl and aryl isocyanates. The latters subsequently react with compounds having an active hydrogen atom, e.g. alcohols, amines, etc to give urethanes, ureas, and other compounds [3,4]. However the behavior of triazoles and tetrazoles, unsubstituted at the nitrogen atom, and of other heterocyclic alcohols has remained unclear to this time.In order to assess the reactivity of the azole-containing alcohols 1a-d and glycol 2 with isocyanates we have carried out their reaction with benzoyl azide (Scheme 1). Since isocyanates are readily formed from acyl azides upon heating in an anhydrous medium [3,4] their initial separation was not necessary. Reactions of compounds 1a-d, 2 with benzoyl azide were carried out on heating in absolute dioxane. It was found that alcohols 1a-d and glycol 2 react without particular complications with the phenyl isocyanate formed during the Curtius rearrangement to yield the N-phenylurethanes 3a-d and 4 (Table 1).

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2-PHENYL-2,1,3-TRIAZOLE-4-CARBOXALDEHYDE AND DERIVATIVES¹

Cited by 21 publications

References 0 publications

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Heterociclos 1,2,3-triazólicos: histórico, métodos de preparação, aplicações e atividades farmacológicas

The curtius reaction in the synthesis of noncondensed polynuclear azoles

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2-PHENYL-2,1,3-TRIAZOLE-4-CARBOXALDEHYDE AND DERIVATIVES1

Cited by 21 publications

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Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Heterociclos 1,2,3-triazólicos: histórico, métodos de preparação, aplicações e atividades farmacológicas

The curtius reaction in the synthesis of noncondensed polynuclear azoles

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2-PHENYL-2,1,3-TRIAZOLE-4-CARBOXALDEHYDE AND DERIVATIVES¹