Asymmetric 1,3-Dipolar Cycloaddition of Nitrile Oxides Generated in situ by Direct Oxidation of Aldoximes

Several 3,5-disubstituted isoxazoles were obtained in good yields by regiospecific 1,3-dipolar cycloaddition reactions between aromatic nitrile oxides, generated in situ from the corresponding hydroxyimidoyl chlorides, with non-symmetrical activated alkynes in the presence of catalytic amounts of copper(I) iodide. Effects of 3,5-disubstituted isoxazoles on nitric oxide and reactive oxygen species generation in Arabidopsis tissues was studied using specific diaminofluoresceine dyes as fluorescence indicators.

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ChemInform Abstract: An Efficient Entry to 1,2-Benzisoxazoles via 1,3-Dipolar Cycloaddition of in situ Generated Nitrile Oxides and Benzyne.

ChemInform ◽

10.1002/chin.201043127 ◽

2010 ◽

Vol 41 (43) ◽

pp. no-no

Author(s):

Christian Spiteri ◽

Christopher Mason ◽

Fengzhi Zhang ◽

Dougal J. Ritson ◽

Pallavi Sharma ◽

...

Keyword(s):

Dipolar Cycloaddition ◽

Nitrile Oxides

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Synthesis of isoxazole conjugates of sugars via 1,3-dipolar cycloaddition

Canadian Journal of Chemistry ◽

10.1139/v07-145 ◽

2008 ◽

Vol 86 (2) ◽

pp. 138-141 ◽

Cited By ~ 3

Author(s):

Vipraja V Vaidya ◽

Karuna S Wankhede ◽

Manikrao M Salunkhe ◽

Girish K Trivedi

Keyword(s):

Click Chemistry ◽

Dipolar Cycloaddition ◽

Dipolar Cycloadditions ◽

Nitrile Oxides ◽

High Degree

Isoxazole conjugates of sugar have been synthesized by the aid of 1,3-dipolar cycloaddition in a click chemistry approach. The sugar-derived propargyl ethers underwent 1,3-dipolar cycloadditions smoothly with in situ generated nitrile oxides from aromatic oximes in good yields. The reaction exhibited a high degree of regioselectivity.Key words: isoxazole conjugates, 1,3-dipolar cycloadditions, nitrile oxides.

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Nitrile Oxide 1,3-Dipolar Cycloaddition by Dehydration of Nitromethane Derivatives Under Continuous Flow Conditions

Australian Journal of Chemistry ◽

10.1071/ch11079 ◽

2011 ◽

Vol 64 (10) ◽

pp. 1397 ◽

Cited By ~ 10

Author(s):

Malte Brasholz ◽

Simon Saubern ◽

G. Paul Savage

Keyword(s):

Continuous Flow ◽

Reaction Times ◽

Nitro Compounds ◽

Dipolar Cycloaddition ◽

Flow Conditions ◽

Nitrile Oxides ◽

Aliphatic Nitrile ◽

By Products ◽

Flow Techniques

Aliphatic nitrile oxides were generated in situ, by dehydration of terminal nitro compounds, and reacted with dipolarophiles using continuous flow techniques to afford substituted isoxazolines. The yields of cycloadducts were comparable with traditional flask-based reactions but reaction times were much shorter. In-line scavenger cartridges conveniently removed by-products and unreacted reagents to give almost pure crude products. The process was demonstrated up to gram scale.

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ChemInform Abstract: An Improved, Easy and Efficient Method for the Generation of Nitrile Oxides from Nitronates for in situ 1,3-Dipolar Cycloaddition.

ChemInform ◽

10.1002/chin.199938137 ◽

2010 ◽

Vol 30 (38) ◽

pp. no-no

Author(s):

Jing-Yuan Liu ◽

Ming-Chung Yan ◽

Wen-Wei Lin ◽

Lian-Yong Wang ◽

Ching-Fa Yao

Keyword(s):

Efficient Method ◽

Dipolar Cycloaddition ◽

Nitrile Oxides

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Enolate-mediated 1,3-dipolar cycloaddition reactions of allyl ketones with nitrile oxides: direct access to 3,5-disubstituted isoxazolines

Organic & Biomolecular Chemistry ◽

10.1039/c6ob02025a ◽

2016 ◽

Vol 14 (42) ◽

pp. 9985-9988 ◽

Cited By ~ 4

Author(s):

Wenjun Li ◽

Xiao Zhou ◽

Zhenyan Shi ◽

Yang Liu ◽

Zhantao Liu ◽

...

Keyword(s):

Direct Access ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

Nitrile Oxides ◽

High Yields

TMG-catalyzed [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of allyl ketones with in situ generated nitrile oxides have been developed. This strategy could generate 3,5-disubstituted isoxazolines in high yields and regioselectivities.

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