In:
Asian Journal of Chemistry, Asian Journal of Chemistry, Vol. 32, No. 8 ( 2020), p. 1886-1894
Abstract:
[3+2] Cycloadditions of nitrones as three-atom components to alkenes yield isoxazolidine cycloadducts, which on chemical transformations can be converted to bioactive compounds. The [3+2] cycloadditions route thus provides conversion of simple natural products to more complex naturally occurring bioactive
nitrogen heterocycles, and close analogues. As α,β-unsaturated amides abundantly occur as natural products, [3+2] cycloadditions of nitrones with simpler α,β-unsaturated amides were studied to get information about reactivity profiles. The reactions of C-(4-chlorophenyl)-N-methyl nitrone as
three-atom component to cinnamic acid anilides were investigated. The 3,4-trans-4,5-trans-4- carboxanilido-2-methyl-3,5-diaryl isoxazolidines were the major cycloadducts; the diastereoisomeric
3,4-cis-4,5-trans-4-carboxanilido-2-methyl-3,5-diaryl isoxazolidines and regioisomeric 3,4-trans-4,5- trans-5-carboxanilido-2-methyl-3,4-diaryl isoxazolidines were obtained as minor cycloadducts. The
cycloadducts were characterized by NMR studies and XRD analysis.
Type of Medium:
Online Resource
ISSN:
0975-427X
,
0970-7077
DOI:
10.14233/ajchem.2020.22695
Language:
English
Publisher:
Asian Journal of Chemistry
Publication Date:
2020
detail.hit.zdb_id:
3140213-6
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