Heck-type hydroarylations and 1,3-dipolar cycloaddition reactions of new tricyclic hydrazones

2010 ◽  
Vol 88 (4) ◽  
pp. 323-330 ◽  
Author(s):  
Melek Gul ◽  
Nuket Ocal
Keyword(s):  
Biological Activity ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Potential Biological Activity

The C–C coupling of the new tricyclic hydrazones 3–7 with aryl and heteroaryl halides gave under reductive Heck conditions the tricyclic 1-(arylideneamino)pyrolidine-2,5-diones 8–11a, 9–11b, 10c, and 12. The [3+2] cycloadditions of 3–7 with p-chlorophenyl nitrile oxide (13) yielded the bridged isoxazoline derivatives 14–18 with potential biological activity.

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

Mechanism of 1,3-dipolar cycloaddition reactions of indan-1-one enamines with aryl nitrile oxide: a DFT analysis

2016 ◽  
Vol 13 (9) ◽  
pp. 1629-1634
Author(s):  
Amir Khojastehnezhad ◽  
Hossein Eshghi ◽  
Farid Moeinpour ◽  
Arastou Raoufi
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

scholarly journals 1,3-Dipolar Cycloaddition Reactions of meso-Tetra(2’- thienyl)porphyrins with a Nitrile Oxide

2013 ◽  
Author(s):  
Patrícia B. Momo ◽  
Ricardo B. Ayres ◽  
Timothy J. Brocksom ◽  
Kleber T. de Oliveira
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

Regio- and diastereo-selective formation of Isoxazoline Derivatives by Lewis acid Mediated 1,3-dipolar Cycloaddition Reactions of Nitrile Oxide

2007 ◽  
Vol 2007 (7) ◽  
pp. 394-396 ◽  
Author(s):  
Saori Hayashi ◽  
Akira Mori ◽  
Masatoshi Nishina ◽  
Masanori Sumimoto ◽  
Kenzi Hori ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Cycloaddition Reaction ◽  
Chiral Auxiliary ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Magnesium Perchlorate ◽  
Nitrile Oxides ◽  
Selective Formation

In the presence of magnesium perchlorate, 1,3-dipolar cycloaddition reactions of nitrile oxides to crotonamide bearing 4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-one as the chiral auxiliary proceeded with a regio- and diastereo-selective manner to afford the corresponding chiral 2-isoxazoline. The mechanisms underlying the diastereoface selection in the cycloaddition reaction were investigated using the B3LYP/6-31G* level of theory.

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