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Questions and Answers
What product is formed in Entry 1 with azide N3 and starting material N?
NO2
What is the yield percentage for the product formed in Entry 3 with azide OCH3?
94
Which characteristic peak is observed at approximately 120±3 ppm in the synthesized molecules?
In the synthesis of benzotriazole-triazole conjugates, copper catalyzed reactions exclusively deliver 1,4-disubstituted products.
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What is the name of the synthesis protocol used to create the benzotriazole-triazole conjugates?
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What are some of the biological properties associated with benzotriazole and triazole compounds?
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The CuAAC reaction primarily involves the catalytic moiety Cu(II).
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The CuAAC reaction favors the synthesis of 1,4-disubstituted-1,2,3-triazoles in _____ yields.
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What is the melting point range of compound 3c?
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What is the chemical formula of the compound with the HRMS calc.for C9H7FN3O?
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In which solvent were the 1H NMR and 13C NMR of benzotriazole-triazole conjugates recorded?
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The 13C NMR chemical shift values are given in parts per billion (ppb).
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The compound 5e is a ____ solid with a melting point of 140-142 °C.
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What is the yield observed when the reaction was carried out with copper acetate as a catalyst?
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Which solvent showed a higher yield in the reaction - methanol or water?
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Increasing the concentration of the catalyst to 5.0 mol% improved the product yield. (True/False)
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What was the yield of product when the reaction was optimized using the above-mentioned conditions with aryl azide 4a and alkyne 3a? _____%
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What is the regioselectivity observed in the current protocol for the copper-acetate catalyzed CuAAC reaction?
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What is the main focus of the review by Sathish Kumar S and Kavitha P 2013?
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Which compound was synthesized and evaluated for antimicrobial activity by Ashok D et al. in 2020?
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The synthesis and evaluation of benzotriazole derivatives as novel antifungal agents was done by Shah J J et al. in ____.
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Caliendo et al. in 1995 conducted a study on benzotriazole derivatives structurally related to ibuprofen.
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Match the following compounds with their activities:
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Study Notes
Benzotriazole-Triazole Conjugates Synthesis
- The synthesis of novel benzotriazole-triazole conjugates via copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction between benzotriazole alkynes and aryl azides has been described.
Importance of Benzotriazole and Triazole
- Benzotriazole and triazole are significant pharmacophores with various biological activities, such as anti-convulsant, anti-microbial, anti-fungal, anti-inflammatory, and anti-cancer properties.
- Benzotriazole has been recognized as a useful building block for the synthesis of biologically active heterocyclic compounds.
CuAAC Reaction
- The CuAAC reaction is a reliable method for the synthesis of 1,4-disubstituted-1,2,3-triazoles in high yields.
- The reaction proceeds with Cu(I) species as the catalytic moiety, and can be executed with direct use of Cu(I) salts or in situ generation of Cu(I) species.
Experimental Procedure
- The synthesis of hydroxybenzotriazole alkyne involves the reaction of 1-hydroxybenzotriazole with potassium carbonate and propargyl bromide in acetone.
- The reaction mixture is refluxed for 1-3 hours, and the resulting product is purified using column chromatography.
Spectroscopic Data
- The synthesized compounds (3a-e) were characterized by 1H NMR, 13C NMR, and mass spectral studies.
- The compounds (5a-n) were characterized by 1H NMR, 13C NMR, and HRMS (TOF MS ES+).
Compounds Synthesized
- 15 compounds (5a-n) were synthesized, with varying substituents on the benzotriazole and triazole rings.
- The physical properties and spectroscopic data of the synthesized compounds are reported.### Synthesis of Benzotriazole-Triazole Conjugates
- The synthesis of benzotriazole-triazole conjugates was achieved through the azide-alkyne cycloaddition (CuAAC) reaction.
- The reaction involved the coupling of benzotriazole alkynes and aryl azides in the presence of a copper catalyst.
Optimization of Reaction Conditions
- The reaction was optimized using different catalysts, solvents, and reaction times.
- The best conditions were found to be using Cu(OAc)2 (1 mol%) in methanol at room temperature, which gave a 70% yield.
- No product formation was observed in the absence of a catalyst or when using Cu(I) oxide as the catalyst.
- The use of Cu(I) iodide and CuSO4.5H2O as catalysts gave yields of 51% and 57%, respectively.
Substrate Scope
- The optimized reaction conditions were applied to a range of substrates with different electron-donating and electron-withdrawing groups.
- The reaction was successful in all cases, giving yields ranging from 65% to 98%.
- The use of benzotriazole alkynes with electron-withdrawing and electron-donating groups did not have a significant effect on the yield.
- The regioselectivity of the reaction was found to be in favor of the 1,4-disubstituted product.
Spectroscopic Characterization
- The products were characterized by 1H NMR and 13C NMR spectroscopy.
- The characteristic singlet peaks in the 1H NMR spectrum at δ 9.2 ppm and 5.81 ppm confirm the formation of the triazolyl proton and methylene protons, respectively.
- The 13C NMR spectrum shows a characteristic peak at δ 119 ppm, which confirms the formation of the 1,4-disubstituted product.### Benzotriazole-Triazole Conjugates
- A novel series of benzotriazole-triazole conjugates have been synthesized from a wide range of benzotriazole alkynes and aryl azides using a copper-catalyzed azide-alkyne cycloaddition route.
- The protocol avoids the use of reducing agents and shows complete regioselectivity in favor of 1,4-disubstituted products.
Synthesis of 1-Hydroxybenzotriazoles
- The synthesis of 1-hydroxybenzotriazoles (2a-e) involves the addition of o-halonitrobenzene to a stirred solution of hydrazine hydrate, sodium carbonate, and ethanol at 90°C.
- The completion of the reaction is monitored using TLC, and the resultant solution is acidified with 1N HCl.
- The precipitates formed are collected, filtered, and dried, and the product is purified by recrystallization from ethanol.
Reactions and Conditions
- The reaction conditions involve the use of hydroxybenzotriazole alkyne (1.5 mmol), aryl azide (1 mmol), copper acetate (1 mol%), and methanol (1-2 mL).
- The yields of pure isolated products are reported, and the products are characterized by 1H NMR, 13C NMR, and mass spectroscopy.
Previous Research
- Previous studies have reported the synthesis and biological activities of benzotriazole and triazole derivatives, including antimicrobial and antifungal agents.
- The literature records the exclusive formation of 1,4-disubstituted products using copper-catalyzed reactions, while ruthenium-catalyzed protocols deliver 1,5-disubstituted products as major products.
Applications
- The synthesized compounds have potential applications in the field of medicinal chemistry, including antitubercular, antiviral, and anticancer activities.
- The benzotriazole-triazole conjugates may also be used as antimicrobial agents, and further biological screening is currently underway.
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Description
This quiz covers the synthesis of benzotriazole-triazole conjugates, including reaction conditions, product formation, and yield percentages. It also touches on the characteristic peaks observed in the synthesized molecules and the copper-catalyzed reaction mechanism.
