[3+2] Cycloadditions: Part XXXV. Selective Cycloadditions of C-(4-Chlorophenyl)-N-methyl Nitrone to Cinnamic Acid Anilides

Sumana Sengupta1,2,*, Avijit Banerji2,3, Thierry Prangé4, Alain Neuman5 and Jayram Hazra3

1Department of Chemistry, Chandernagore College, Chandernagore, Hooghly-712136, India

2Centre of Advanced Studies on Natural Products including Synthesis, Department of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata-700009, India

3Central Ayurveda Research Institute for Drug Development, Kolkata-700091, India

4Laboratoire de Cristallographie et RMN Biologiques, Faculté de pharmacie, 4, Av de l'Observatoire, 75006 Paris, France

5UFR SMBH - Université Paris 13, 74, rue Marcel Cachin 93000 Bobigny, France

*Corresponding author: E-mail: sngsumana@gmail.com

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.

Keywords

[3+2] Cycloaddition, Isoxazolidine, Nitrone, Cinnamic acid anilides.

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