Organic Chemistry: Benzotriazole-Triazole Conjugates Synthesis
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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?

  • 110±3
  • 120±5
  • 133±3
  • 120±3 (correct)

    • In the synthesis of benzotriazole-triazole conjugates, copper catalyzed reactions exclusively deliver 1,4-disubstituted products.

    <p>True</p> Signup and view all the answers

    What is the name of the synthesis protocol used to create the benzotriazole-triazole conjugates?

    <p>Copper-catalyzed Azide-Alkyne cycloaddition click protocol (CuAAC)</p> Signup and view all the answers

    What are some of the biological properties associated with benzotriazole and triazole compounds?

    <p>Anticancer</p> Signup and view all the answers

    The CuAAC reaction primarily involves the catalytic moiety Cu(II).

    <p>False</p> Signup and view all the answers

    The CuAAC reaction favors the synthesis of 1,4-disubstituted-1,2,3-triazoles in _____ yields.

    <p>high</p> Signup and view all the answers

    What is the melting point range of compound 3c?

    <p>48-50 °C</p> Signup and view all the answers

    What is the chemical formula of the compound with the HRMS calc.for C9H7FN3O?

    <p>C9H7FN3O</p> Signup and view all the answers

    In which solvent were the 1H NMR and 13C NMR of benzotriazole-triazole conjugates recorded?

    <p>DMSO-d6</p> Signup and view all the answers

    The 13C NMR chemical shift values are given in parts per billion (ppb).

    <p>False</p> Signup and view all the answers

    The compound 5e is a ____ solid with a melting point of 140-142 °C.

    <p>Brown</p> Signup and view all the answers

    What is the yield observed when the reaction was carried out with copper acetate as a catalyst?

    <p>60%</p> Signup and view all the answers

    Which solvent showed a higher yield in the reaction - methanol or water?

    <p>Methanol</p> Signup and view all the answers

    Increasing the concentration of the catalyst to 5.0 mol% improved the product yield. (True/False)

    <p>False</p> Signup and view all the answers

    What was the yield of product when the reaction was optimized using the above-mentioned conditions with aryl azide 4a and alkyne 3a? _____%

    <p>62</p> Signup and view all the answers

    What is the regioselectivity observed in the current protocol for the copper-acetate catalyzed CuAAC reaction?

    <p>1,4-disubstituted</p> Signup and view all the answers

    What is the main focus of the review by Sathish Kumar S and Kavitha P 2013?

    <p>biological applications of triazole derivatives</p> Signup and view all the answers

    Which compound was synthesized and evaluated for antimicrobial activity by Ashok D et al. in 2020?

    <p>1,2,3-Triazole</p> Signup and view all the answers

    The synthesis and evaluation of benzotriazole derivatives as novel antifungal agents was done by Shah J J et al. in ____.

    <p>2015</p> Signup and view all the answers

    Caliendo et al. in 1995 conducted a study on benzotriazole derivatives structurally related to ibuprofen.

    <p>False</p> Signup and view all the answers

    Match the following compounds with their activities:

    <p>Benzimidazole-coumarin conjugates = Anti-hepatitis C virus Coumarin-benzotriazole hybrids = Anti-tubercular 1,2,4-triazole derivatives = Antioxidant</p> Signup and view all the answers

    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.

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