Computational exploration of the 1,3‐dipolar cycloaddition reaction of 7‐isopropylidenebenzonorbornadiene with nitrile oxide and cyclic nitrone derivatives

Highly functionalised potential neuraminidase (NA) inhibitors, analogues of peramivir, were synthesised via a new and versatile method starting from a stereoselective 1,3-dipolar cycloaddition reaction between the nitrile oxide derived from 2-ethylbutanal and the commercially available and inexpensive cyclopentadiene and 1,3-cyclohexadiene, which afforded the isoxazolino-cyclopentene or cyclohexene intermediates, respectively. The subsequent reaction of the C=C bond in different conditions allowed the functionalisation of the five (or six) membered carbon nucleus. Further functionalised derivatives displaying an amino and a hydroxyl group were achieved via the final opening of the isoxazoline ring.

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Reactivity of 2-Methylene-1,3-dicarbonyl Compounds. 1,3-Dipolar Cycloaddition Reaction with Nitrile Oxide.

ChemInform ◽

10.1002/chin.200310132 ◽

2003 ◽

Vol 34 (10) ◽

Author(s):

Masahige Yamauchi

Keyword(s):

Cycloaddition Reaction ◽

Nitrile Oxide ◽

Dipolar Cycloaddition ◽

Dicarbonyl Compounds

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A quantum-chemical DFT study of the mechanism and regioselectivity of the 1,3-dipolar cycloaddition reaction of nitrile oxide with electron-rich ethylenes

International Journal of Quantum Chemistry ◽

10.1002/qua.25540 ◽

2017 ◽

Vol 118 (11) ◽

pp. e25540 ◽

Cited By ~ 6

Author(s):

Wassila Yahia ◽

Abdelmalek Khorief Nacereddine ◽

Messaoud Liacha ◽

Abdelhafid Djerourou

Keyword(s):

Quantum Chemical ◽

Cycloaddition Reaction ◽

Nitrile Oxide ◽

Dft Study ◽

Dipolar Cycloaddition

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Investigating the reaction pathways of chemical functionalization of C20 fullerene by nitrile oxide and azide; A computational study

Journal of Theoretical and Computational Chemistry ◽

10.1142/s0219633618500037 ◽

2018 ◽

Vol 17 (01) ◽

pp. 1850003

Author(s):

Sakineh Asghari ◽

Ali Asghar Gouran ◽

Davood Farmanzadeh ◽

Tahereh Abdollahi

Keyword(s):

Functional Group ◽

Computational Study ◽

Cycloaddition Reaction ◽

Nitrile Oxide ◽

Dipolar Cycloaddition ◽

Hydrazoic Acid ◽

Density Of State ◽

Electronic Density ◽

C20 Fullerene ◽

Oxide Group

In this study, the interactions between nitrile oxide (fulminic acid) and azide (hydrazoic acid) with the C[Formula: see text] fullerene were investigated and their priority in reacting and functionalizing surface of this fullerene were compared with each other. The results show that the 1,3-dipolar cycloaddition reaction between fulminic acid and C[Formula: see text] fullerene could occur faster than this reaction by hydrazoic acid. Therefore, nitrile oxide group as a dipole is much preferred compared to the azide functional group in reacting with the surface of C[Formula: see text] fullerene. In addition, the calculated adsorption energy and electronic density of state, DOS plots for the related species confirmed that the C[Formula: see text] fullerene can be used as sensors for sensing the hydrazoic acid and fulminic acid molecules.

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