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Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents

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Abstract

Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80 °C. DES/TBAI system was reused up to five consecutive times.

Graphic abstract

Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.

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Acknowledgements

We are thankful to Persian Gulf University Research Council for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    Mohammadesmaeil Moayyed

  2. Marine Chemistry Department, Faculty of Marine Science and Technology, Persian Gulf University, Bushehr, 75169, Iran

    Dariush Saberi

  3. Fisheries and Aquaculture Department, Faculty of Agriculture and Natural Resources, Persian Gulf University, Bushehr, 75169, Iran

    Dariush Saberi

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  1. Mohammadesmaeil Moayyed
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  2. Dariush Saberi
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Correspondence to Dariush Saberi.

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Moayyed, M., Saberi, D. Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents. J IRAN CHEM SOC 18, 445–455 (2021). https://doi.org/10.1007/s13738-020-02039-1

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