Spiro Isoxazolines via Nitrile Oxide 1,3-Dipolar Cycloaddition Reactions

Savage, G. Paul

doi:10.2174/138527210791616812

Cited by 49 publications

(13 citation statements)

References 146 publications

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“…Five new isoxazolines containing one or two bithienyl moieties were obtained via [Ru]- or 15-crown-5/NaOH catalyzed isomerization of 5-allyl-2,2'-bithiophene 9 to 5-(1-propenyl)-2,2'-bithiophene and then 1,3-DC of nitrile oxide to 10 (Scheme 5). The range of reviews on the synthesis of isoxazolines via the addition of nitrile oxides to alkenes is very extensive and includes many monographic reports [42,43,44,45], and our papers [46,47,48]. The methods of preparation of numerous pure, stable nitrile oxides [49] or generated in situ [50,51] have been also described.…”

Section: Resultsmentioning

confidence: 99%

Multifaceted Strategy for the Synthesis of Diverse 2,2'-Bithiophene Derivatives

et al. 2015

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New catalytically or high pressure activated reactions and routes, including coupling, double bond migration in allylic systems, and various types of cycloaddition and dihydroamination have been used for the synthesis of novel bithiophene derivatives. Thanks to the abovementioned reactions and routes combined with non-catalytic ones, new OPEN ACCESSMolecules 2015, 20 4566 acetylene, butadiyne, isoxazole, 1,2,3-triazole, pyrrole, benzene, and fluoranthene derivatives with one, two or six bithiophenyl moieties have been obtained. Basic sources of crucial substrates which include bithiophene motif for catalytic reactions were 2,2'-bithiophene, gaseous acetylene and 1,3-butadiyne.

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Section: Resultsmentioning

confidence: 99%

Multifaceted Strategy for the Synthesis of Diverse 2,2'-Bithiophene Derivatives

et al. 2015

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“…For mono-substituted or 1,1-disubstituted alkenes the regiochemistry of the nitrile oxide cycloaddition followed the expected outcome in which the oxygen of the nitrile oxide became attached to the more substituted end of the double bond [ 41 ]. This regiochemical orientation was established from the 1 H NMR chemical shifts for the cycloadduct isoxazoline ring protons.…”

Section: Resultsmentioning

confidence: 99%

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

Harding¹,

Marcuccio²,

Savage³

2012

Beilstein J. Org. Chem.

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SummaryAn aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction.

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“…were the first to introduce the general concept for the synthesis of isoxazoline rings [48–49] . The 1,3‐dipolar cycloaddition [25,50–54] reaction played a significant role in the formation of isoxazolines using different oximes [55–56] or nitro compounds [57–58] . Various synthetic methods have been reported for the synthesis of five‐membered cyclic isoxazolines with and without metal‐catalyzed synthetic routes.…”

Section: Synthetic Approaches Toward Isoxazolinesmentioning

confidence: 99%

2‐Isoxazolines: A Synthetic and Medicinal Overview

Kumar

Shankar

2020

ChemMedChem

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Isoxazolines are nitrogen‐ and oxygen‐containing five‐membered heterocyclic scaffolds with extensive biological activities. This framework can be readily obtained in good to excellent yields through 1,3‐dipolar cycloaddition between nitrones with alkynes or allenes, aryl/alkyl halides, alkynes, and oxaziridines under mild conditions. This scaffold has been an emerging area of interest for many researchers given their wide range of bioactivities. Herein we review synthetic strategies toward isoxazolines and the role these efforts have had in enhancing the biological activity of natural products and synthetic compounds such as antitubercular agents, COX‐1 inhibitors, COX‐2 inhibitors (e. g., valdecoxib), nicotinic receptor modulators, and MIF inhibitors. With a focus on efforts from 2010 onward, this review provides in‐depth coverage of the design and biological evaluation of isoxazoline systems and their impact on various pathologies.

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Spiro Isoxazolines via Nitrile Oxide 1,3-Dipolar Cycloaddition Reactions

Cited by 49 publications

References 146 publications

Multifaceted Strategy for the Synthesis of Diverse 2,2'-Bithiophene Derivatives

Multifaceted Strategy for the Synthesis of Diverse 2,2'-Bithiophene Derivatives

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

2‐Isoxazolines: A Synthetic and Medicinal Overview

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