A New Reaction of Ethylenic Double Bonds

Quilico, A.; D'Alcontres, Guglielmo Stagno; Grünanger, Paolo

doi:10.1038/166226a0

Cited by 52 publications

(25 citation statements)

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“…[3] Nitrile oxides have been widely utilized as dipoles in 13DC reactions because they allow the rapid preparation of isoxazolines and isoxazoles by reactions with alkenes and alkynes, respectively. [4] This method is fairly general and complements classical condensation methods because of its greater functional group compatibility and the use of milder The 13DC reactions of nitrile oxides have also been theoretically studied. [5][6][7][8] The regioselectivity of the 13DC reactions of benzonitrile N-oxides (NBOs) with ED alkynes and alkenes has been studied by Hu and Houk.…”

Section: Introductionmentioning

confidence: 99%

An Analysis of the Regioselectivity of 1,3‐Dipolar Cycloaddition Reactions of Benzonitrile N‐Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices

2009

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The regioselectivity of the 1,3‐dipolar cycloaddition (13DC) reactions of benzonitrile N‐oxides (BNOs) with electrophilic and nucleophilic alkenes has been analyzed by using global and local nucleophilicity and electrophilicity reactivity indices defined within the conceptual DFT. The BNOs react with electron‐deficient and electron‐rich ethylenes, but the regioselectivities of these polar reactions are different. Whereas the reactions with electron‐rich ethylenes are completely regioselective, yielding 5‐isoxazolines, a change in the regioselectivity is observed in the reactions with electron‐deficient ethylenes, which yield a mixture of 4‐ and 5‐isoxazolines. Analysis of the energies, geometries, and electronic structures of the transition‐state structures involved in the 13DC reactions between the BNOs and two electronically activated ethylenes are in complete agreement with the analysis of the global and local electrophilicity and nucleophilicity reactivity indices.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Introductionmentioning

confidence: 99%

An Analysis of the Regioselectivity of 1,3‐Dipolar Cycloaddition Reactions of Benzonitrile N‐Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices

2009

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“…1) and completely saturated analog is isoxazolidine 1e ( fig. 1) [4][5]. 2), nitric oxide donor furaxan 14 ( fig.…”

Section: Introductionmentioning

confidence: 99%

Isoxazole – A Potent Pharmacophore

Chikkula¹,

Raja

2017

Int J Pharm Pharm Sci

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Isoxazole is an azole with an oxygen atom next to the nitrogen. Isoxazole rings are found in some natural products, such as ibotenic acid and also found in a number of drugs, including COX-2 inhibitor valdecoxib. Furoxan, a nitric oxide donor is containing isoxazolyl group and found in many β-lactamase resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. The synthetic androgenic steroid danazol also has an isoxazole ring. The substituted isoxazoles are well developed in literature to possess significant biological activities. The disubstituted and trisubstituted isoxazoles have been reported to exhibit broad range of biological activities such as antimicrobial activity, analgesic activity, anti-inflammatory activity, antioxidant activity, anticancer activity, CNS (central nervous system) activity, antitubercular activity and miscellaneous activities like GABA (γ-amino butyric acid) agonistic activity, inhibitory activity, antihypertensive activity, and glutamate transporter activity. The present review summarizes up to date information of various biological activities of isoxazole analogs.

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“…[57] Since then, 1,3-dipolar cycloadditions of nitrile oxides have became an important approach to isoxazoles. Nitrile oxides can undergo dimerization to give furoxans, the rate of this process being strongly dependent on the nature of the nitrile oxide substituent.…”

Section: Cycloadditions Of Nitrile Oxidesmentioning

confidence: 99%

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Piñeiro

Melo

2009

Eur J Org Chem

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The review describes the use of microwave technology to carry out 1,3-dipolar cycloaddition reactions, an important tool for the construction of five-membered heterocycles. Microwave methodology can be applied to generate 1,3-dipoles (nitrones, nitrile oxides, azomethine ylides, azomethine imines, nitrile imines, azides, carbonyl ylides) and to promote the subsequent cycloaddition and usually avoids harsh reaction conditions. This nonconventional energy source is able

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A New Reaction of Ethylenic Double Bonds

Cited by 52 publications

References 0 publications

An Analysis of the Regioselectivity of 1,3‐Dipolar Cycloaddition Reactions of Benzonitrile N‐Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices

An Analysis of the Regioselectivity of 1,3‐Dipolar Cycloaddition Reactions of Benzonitrile N‐Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices

Isoxazole – A Potent Pharmacophore

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

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