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

2008 ◽  
Vol 86 (2) ◽  
pp. 138-141 ◽  
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.

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

2002 ◽  
Vol 31 (11) ◽  
pp. 1112-1113 ◽  
Author(s):  
Masamichi Tsuji ◽  
Yutaka Ukaji ◽  
Katsuhiko Inomata
Keyword(s):  
Dipolar Cycloaddition ◽  
Direct Oxidation ◽  
Nitrile Oxides

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

2021 ◽  
Vol 25 ◽  
Author(s):  
Joaquín Plumet
Keyword(s):  
Carbonyl Compounds ◽  
Critical Discussion ◽  
Aldol Reactions ◽  
Dipolar Cycloaddition ◽  
Hydroxy Ketone ◽  
Unsaturated Ketones ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Water Media ◽  
Synthetic Intermediates

: 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.

1,3-Dipolar Cycloadditions of a Chiral Oxazolidinone With Nitrones and Nitrile Oxides

1995 ◽  
Vol 48 (9) ◽  
pp. 1511 ◽  
Author(s):  
SG Pyne ◽  
J Safaei-G ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Hydrogen Atmosphere ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
The Novel ◽  
X Ray ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Exocyclic Methylene

The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered π-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered π-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.

A New Route to Nitrile Oxides from Primary Alkylhalides for in situ Dipolar Cycloadditions

Synlett ◽  
1998 ◽  
Vol 1998 (4) ◽  
pp. 385-386 ◽  
Author(s):  
Dilipkumar Maiti ◽  
Pranab K. Bhattacharya
Keyword(s):  
Dipolar Cycloadditions ◽  
Nitrile Oxides

Cross 1,3-dipolar cycloadditions of C,N-cyclic azomethine imines with an N-benzyl azomethine ylide: facile access to fused tricyclic 1,2,4-hexahydrotriazines

2019 ◽  
Vol 17 (2) ◽  
pp. 244-247 ◽  
Author(s):  
Kai-Kai Wang ◽  
Yan-Li Li ◽  
Zhan-Yong Wang ◽  
Meng-Wei Hu ◽  
Ting-Ting Qiu ◽  
...  
Keyword(s):  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Azomethine Imines

A cross 1,3-dipolar cycloaddition of two different ylides between C,N-cyclic azomethine imines with an in situ generated non-stabilized azomethine ylide from an N-benzyl precursor is reported.

1,3-Dipolar cycloadditions of nitrile oxides with 7-oxa- and 7-azabenzonorbornadienes

2014 ◽  
Vol 92 (7) ◽  
pp. 635-639 ◽  
Author(s):  
Jaipal R. Nagireddy ◽  
Emily Carlson ◽  
William Tam
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Biological Testing ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Anti Cancer ◽  
Efficient Construction ◽  
Cancer Activity

Dipolar cycloaddition reactions allow for the efficient construction of five-membered heterocycles, often with diverse medicinal applications. We examined the 1,3-dipolar cycloaddition of 7-oxabenzonorbornadienes and 7-azabenzonorbornadienes with acetonitrile oxide and benzonitrile oxide, achieving an assortment of heterobicycle-fused isoxazolines with good to excellent yields. All isoxazolines were consistently directed to the exo face of the bicyclic framework with complete stereoselectivity. Preliminary biological testing of the adducts also showed positive anti-cancer activity, suggesting their potential pharmaceutical utility.

An efficient entry to 1,2-benzisoxazoles via 1,3-dipolar cycloaddition of in situ generated nitrile oxides and benzyne

2010 ◽  
Vol 8 (11) ◽  
pp. 2537 ◽  
Author(s):  
Christian Spiteri ◽  
Christopher Mason ◽  
Fengzhi Zhang ◽  
Dougal J. Ritson ◽  
Pallavi Sharma ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Nitrile Oxides

In Situ Generation of Nitrile Oxides from NaCl–Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition

2018 ◽  
Vol 21 (1) ◽  
pp. 315-319 ◽  
Author(s):  
Guodong Zhao ◽  
Lixin Liang ◽  
Chi Ho Ethan Wen ◽  
Rongbiao Tong
Keyword(s):  
Dipolar Cycloaddition ◽  
Nitrile Oxides ◽  
In Situ Generation
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