ChemInform Abstract: 1,2,3‐Triazolo‐N‐oxides. Part 2. Synthesis of Substituted 4(5)‐ Ethoxycarbonyl‐1,2,3‐triazolo‐N‐oxides.

Kirillova, L. P.; Shul'gina, V. M.; Shafeev, M. A.; Al'mukhamedov, A. A.; Vereshchagin, L. I.

doi:10.1002/chin.199718163

Cited by 3 publications

(4 citation statements)

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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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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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“…Another transformation of bis(hydrazones), hydrazonoamidoximes, and hydrazonohydrazides yielding 2-aryl-1,2,3-triazoles usually occurs under condensation conditions and is accomplished by the elimination of a leaving group [240,[275][276][277][278][279][280][281][282][283][284][285][286][287][288][289][290][291][292][293][294].…”

Section: Intramolecular Cyclization Of Bis(hydrazones) and Hydrazonoamentioning

confidence: 99%

“…Cyclization of arylhydrazone oximes 223 by dehydration agents (Ac 2 O, SOCl 2 , hydroxylamine-O-sulfonic acid) led to 2-aryl-1,2,3-triazoles in the same manner (Scheme 78) [282][283][284][285][286][287][288][289][290].…”

Section: Intramolecular Cyclization Of Bis(hydrazones) and Hydrazonoamentioning

confidence: 99%

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Chemistry of 1,2,3-triazoles

Dehaen¹

2015

Topics in Heterocyclic Chemistry

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The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community.The series consists of topic related volumes edited by renowned editors with contributions of experts in the field.More information about this series at

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Cu-Catalyzed Multicomponent Reaction of Arylhydrazines with β-Ketoesters and TBN: One-Pot Access to N²-Aryl 1,2,3-Triazole-1-Oxides

Mujahid,

Vara,

Arshad

et al. 2024

J. Org. Chem.

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We report a copper-catalyzed one-pot, multicomponent strategy for the convenient synthesis of N 2 -aryl 1,2,3triazole-1-oxides using arylhydrazines, β-ketoesters, and tert-butyl nitrite. This mild and simple reaction proceeds in an atomeconomic manner with broad substrate scope, affording a variety of N 2 -aryl 1,2,3-triazole-1-oxide derivatives. Other salient features of the reaction are good functional group tolerance, scalability, and product diversification.

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ChemInform Abstract: 1,2,3‐Triazolo‐N‐oxides. Part 2. Synthesis of Substituted 4(5)‐ Ethoxycarbonyl‐1,2,3‐triazolo‐N‐oxides.

Cited by 3 publications

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The curtius reaction in the synthesis of noncondensed polynuclear azoles

The curtius reaction in the synthesis of noncondensed polynuclear azoles

Chemistry of 1,2,3-triazoles

Cu-Catalyzed Multicomponent Reaction of Arylhydrazines with β-Ketoesters and TBN: One-Pot Access to N²-Aryl 1,2,3-Triazole-1-Oxides

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ChemInform Abstract: 1,2,3‐Triazolo‐N‐oxides. Part 2. Synthesis of Substituted 4(5)‐ Ethoxycarbonyl‐1,2,3‐triazolo‐N‐oxides.

Cited by 3 publications

References 0 publications

The curtius reaction in the synthesis of noncondensed polynuclear azoles

The curtius reaction in the synthesis of noncondensed polynuclear azoles

Chemistry of 1,2,3-triazoles

Cu-Catalyzed Multicomponent Reaction of Arylhydrazines with β-Ketoesters and TBN: One-Pot Access to N2-Aryl 1,2,3-Triazole-1-Oxides

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Product

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Cu-Catalyzed Multicomponent Reaction of Arylhydrazines with β-Ketoesters and TBN: One-Pot Access to N²-Aryl 1,2,3-Triazole-1-Oxides