Five-Membered Ring Systems With O and N Atoms

Cordero, Franca M.; Giomi, Donatella; Lascialfari, Luisa

doi:10.1016/b978-0-08-100755-6.00011-9

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2018

2022

Publication Types

Select...

Article3

Book1

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

References 138 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

et al. 2019

View full text Add to dashboard Cite

An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4‐disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X‐ray crystallography.

show abstract

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

et al. 2019

View full text Add to dashboard Cite

show abstract

The Literature of Heterocyclic Chemistry, Part XVI, 2016

Беленький

Evdokimenkova

2018

Advances in Heterocyclic Chemistry

View full text Add to dashboard Cite

Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations

Gerster

Keim

Maas

2022

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

Iminium-functionalized 2,3-dihydroisoxazoles (4-isoxazolines) were prepared in high yields by [3+2] cycloaddition of N-methyl-C-phenylnitrone and acetylenic iminium salts. Conversion of the very hygroscopic cycloadducts into neutral compounds was achieved by hydrolysis or hydride reduction of the iminium functional group. By a thermal rearrangement, the cycloadducts were converted into 2,3-dihydro-1H-imidazolium salts. With C,N-diphenylnitrone as the reaction partner, the expected cycloadduct, a [(2,3-dihydroisoxazol-4-yl)-1-(phenyl)methylene]-N,N-dimethylammonium triflate, could be prepared at −75°C and was characterized by NMR. This product was found to be thermally unstable above −30°C, being converted into an inseparable product mixture. Basic hydrolysis of this mixture afforded a structurally interesting acyclic enaminone/half-aminal, which is likely derived from a 2,3-dihydro-1,3-oxazole.

show abstract

Five-Membered Ring Systems With O and N Atoms

Cited by 4 publications

References 138 publications

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

The Literature of Heterocyclic Chemistry, Part XVI, 2016

Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations

Contact Info

Product

Resources

About