1,3-Dipolar Cycloadditions of Aromatic Nitrile Oxides and Nitrones to 1,1'-(Methylenedi-4,1-phenylene)bismaleimide

1992 ◽  
Vol 57 (9) ◽  
pp. 1982-1992 ◽  
Author(s):  
Usama A. R. Al-Timari ◽  
Lubor Fišera ◽  
Naďa Prónayová
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Aromatic Nitrile

Within the scope of our research aimed at utilization of 1,3-dipolar cycloaddition reactions to heterocycles as well as to pesticide programme we report the 1,3-dipolar cycloaddition of nitrile oxides II, III and nitrones V to bis-maleiimide derivative I.

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.

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.

Synthesis of Chiral Isoxazoline Derivatives by Highly Diastereoface-Selective 1,3-Dipolar Cycloaddition of Nitrile Oxides Mediated by Magnesium Bromide and Ytterbium Trifluoromethanesulfonate

2003 ◽  
Vol 2003 (5) ◽  
pp. 284-286 ◽  
Author(s):  
Hidetoshi Yamamoto ◽  
Sadaka Watanabe ◽  
Masayuki Hasegawa ◽  
Michihiko Noguchi ◽  
Shuji Kanemasa
Keyword(s):  
Lewis Acid ◽  
Equimolar Amount ◽  
Dipolar Cycloaddition ◽  
Magnesium Bromide ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
Aromatic Nitrile

In the presence of an equimolar amount of Lewis acid such as magnesium bromide and ytterbium trifluoromethanesulfonate, 1,3-dipolar cycloaddition reactions of aromatic nitrile oxides to a chiral 3-acryloyl-2-oxazolidinone gave the corresponding chiral 2-isoxazolines in a diastereoselective manner.

Utilisation of Enols of Mono- and Dicarbonyls Compounds in 1,3-Dipolar Cycloaddition Reactions

2003 ◽  
Vol 2003 (5) ◽  
pp. 254-255 ◽  
Author(s):  
Joanna Kurkowska ◽  
Irmina Zadrożna
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
Aromatic Nitrile

2-Isoxazolines were obtained from substituted enols or their ester or ether derivatives in 1,3-dipolar cycloaddition reactions with aliphatic or aromatic nitrile oxides.

scholarly journals 1,3-Dipolar Cycloadditions of Some Nitrilimines and Nitrile Oxides to 3-N,N-Dimethylamino-1 -oxopropene Derivatives

1999 ◽  
Vol 23 (6) ◽  
pp. 360-361
Author(s):  
Khadijah Mohamed Al-Zaydi ◽  
Ebtisam Abdel Aziz Hafez
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Efficient Synthesis ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides

An efficient synthesis of some novel pyrazoles 8a-j, 13a-e, 18a,b, isoxazoles 26a-g, pyrazolo[3,4- d]pyridazines 9a-d and isoxazolo[3,4- d]pyridazines 27a-d via 1,3-dipolar cycloaddition reactions is reported.

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