Open Access[3+2] Cycloadditions: Part XXXV. Selective Cycloadditions of C-(4-Chlorophenyl)-N-methyl Nitrone to Cinnamic Acid Anilides
Author(s) -
S. Sengupta,
Avijit Banerji,
T. Prangé,
A. Neuman,
Jayram Hazra
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22695
Subject(s) - chemistry , nitrone , nitrogen atom , cycloaddition , cinnamic acid , yield (engineering) , reactivity (psychology) , stereochemistry , carbon 13 nmr , organic chemistry , medicinal chemistry , catalysis , ring (chemistry) , medicine , alternative medicine , pathology , metallurgy , materials science
[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] cycloadditionsroute thus provides conversion of simple natural products to more complex naturally occurring bioactivenitrogen heterocycles, and close analogues. As α,β-unsaturated amides abundantly occur as naturalproducts, [3+2] cycloadditions of nitrones with simpler α,β-unsaturated amides were studied to getinformation about reactivity profiles. The reactions of C-(4-chlorophenyl)-N-methyl nitrone asthree-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 diastereoisomeric3,4-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. Thecycloadducts were characterized by NMR studies and XRD analysis.