The 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides in Water Media

Author(s): Joaquín Plumet*

Journal Name: Current Organic Chemistry

Volume 25 , Issue 22 , 2021

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The 1,3-dipolar cycloadditions (DCs) of nitrile oxides (NOs) have been used as a powerful tool in synthetic organic chemistry. The cycloadducts arising from cycloadditions (CAs) of NOs to alkenes and alkynes (2-isoxazolines and isoxazoles respectively) are valuable synthetic intermediates because, among others, their capacity to mask other functionalities including α, β-unsaturated ketones, β-hydroxy carbonyl compounds and 1,3- aminoalcohols. In particular, the β-hydroxy ketone functionality is an illustrative example, making the NOs alkenes CAs reactions a synthetically equivalent methodology of aldol reactions. The vast majority of these reactions are carried out in organic solvents. Nevertheless, the use of water as an alternative solvent has evident advantages on the “Green Chemistry” concept. The critical discussion on the use of water instead of “conventional” solvents in the 1,3-DCs reactions of NOs is the objective of the present review.

Keywords: Dipolar cycloadditions, nitrile oxides, water media, micellar catalysis, kinetics, synthetic applications.

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Article Details

Year: 2021
Published on: 06 September, 2021
Page: [2683 - 2707]
Pages: 25
DOI: 10.2174/1385272825666210906162234
Price: $95

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