Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

2019 ◽  
Vol 17 (3) ◽  
pp. 622-638 ◽  
Author(s):  
Patrick G. McCaw ◽  
U. B. Rao Khandavilli ◽  
Simon E. Lawrence ◽  
Anita R. Maguire ◽  
Stuart G. Collins
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides

The generation of novel 1,2,5-oxathiazole-S-oxide cycloadducts from cycloaddition of nitrile oxide dipoles with α-oxo sulfines generated in situ from α-diazosulfoxides is reported.

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

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.

Cycloadditions of 2,5-dimethyl-3-furannitrile oxide to alkenes and alkynes

1990 ◽  
Vol 55 (10) ◽  
pp. 2481-2492 ◽  
Author(s):  
Eva Jedlovská ◽  
Lubor Fišera ◽  
Anna Balková ◽  
Jaroslav Kováč ◽  
Ladislav Štibrányi
Keyword(s):  
Mndo Method ◽  
Nitrile Oxide ◽  
Dipolar Cycloadditions

Regioselectivity of 1,3-dipolar cycloadditions of 2,5-dimethyl-3-furannitrile oxide (IIa) to alkenes or alkynes is described. Nitrile oxide IIa generated in situ reacts with monosubstituted alkenes or alkynes to give exclusively 5-substituted 3-(5-dimethyl-3 -furyl)-2-isoxazolines IV and isoxazoles V, 2,5-disubstituted alkenes sometimes afforded a mixture of regioisomeric isoxazolines. Reactivity of furannitrile oxides II and III in cycloadditions to ethene was studied by the MNDO method.

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