- Synthesis of 3,5-Disubstituted Isoxazoles through a 1,3-Dipolar Cycloaddition Reaction between Alkynes and Nitrile Oxides Generated from O-Silylated Hydroxamic Acids
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In this paper, we report the regioselective synthesis of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition between alkynyl dipolarophiles and nitrile oxide dipoles generated in-situ from O-silylated hydroxamic acids in the presence of trifluoromethanesulfonic anhydride and NEt3. Thanks to the mild, metal-free and oxidant-free conditions that this strategy offers, the reaction was successfully applied to a wide variety of alkynyl dipolarophiles, demonstrating the tolerance of this approach to diverse functional groups. In particular, we have shown that the method was compatible with biological molecules such as peptides and peptide nucleic acids (PNA). This protocol constitutes another example of metal-free 1,3-dipolar cycloaddition leading to the regioselective formation of isoxazoles.
- Carloni, Laure-Elie,Mohnani, Stefan,Bonifazi, Davide
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supporting information
p. 7322 - 7334
(2019/11/05)
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- One-pot synthesis of precise polyisoxazoles by click polymerization: Copper (I)-catalyzed 1,3-dipolar cycloaddition of nitrile oxides with alkynes
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This article reports a new one-pot method for polymer preparation, which involves double click chemistry. In one pot, two click reactions take place sequentially by adding the reactants step by step. The first click reaction is to produce the monomer for
- Li, Yan,Cheng, Bin
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p. 1645 - 1650
(2013/08/25)
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- REACTION OF PERFLUORINATED NITRILES WITH BENZ- AND TEREPHTHALAMIDOXIMES FOR THE ISOLATION OF MIXED 1,2,4-OXADIAZOLES
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The reaction of perfluorinated nitriles with benz- and terephthalamidoximes afforded amidoximimidates which can form mixed 1,2,4-oxadiazoles in high yield under mild conditions by the action of acid fluorides of perfluorocarboxylic acids.The structure of
- Kabakchi, E. V.,Il'in, V. V.,Ignatenko, A. V.,Ponomarenko, V. A.
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p. 1453 - 1458
(2007/10/02)
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