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.

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.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

scholarly journals Synthesis of Aza-Pterocarpan Analogues via 1,3 Intramolecular Dipolar Cycloadditions in in situ generated Iminoolefins

2013 ◽  
Author(s):  
Julio C.F.Barcellos ◽  
Ayres G. Dias ◽  
José M. Sansano ◽  
Carmen Nájera ◽  
Paulo R. R. Costa
Keyword(s):  
Dipolar Cycloadditions

Nitrile Oxide Cycloaddition Chemistry Using Benzotriazole as a Steric Auxiliary

2005 ◽  
Vol 58 (12) ◽  
pp. 877 ◽  
Author(s):  
G. Paul Savage ◽  
Gregory T. Wernert
Keyword(s):  
Nitrile Oxide

The relatively hindered 2,2-bis(benzotriazol-1-yl)acetonitrile oxide was prepared in situ from the precursor hydroximinoyl chloride, and was allowed to react with dipolarophiles to give rise to several isoxazoles. The benzotriazole substituents acted as steric auxiliaries to prevent unwanted dimerization of the nitrile oxide to the furoxan by-product.

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.

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