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Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

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

https://doi.org/10.14233/ajchem.2020.22695
Sumana Sengupta
1 Department of Chemistry, Chandernagore College, Chandernagore, Hooghly-712136, India 2 Centre of Advanced Studies on Natural Products including Synthesis, Department of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata-700009, India
Avijit Banerji
2 Centre of Advanced Studies on Natural Products including Synthesis, Department of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata-700009, India 3 Central Ayurveda Research Institute for Drug Development, Kolkata-700091, India
Thierry Prangé
Laboratoire de Cristallographie et RMN Biologiques, Faculté de pharmacie, 4, Av de l'Observatoire, 75006 Paris, France
Alain Neuman
UFR SMBH - Université Paris 13, 74, rue Marcel Cachin 93000 Bobigny, France
Jayram Hazra
Central Ayurveda Research Institute for Drug Development, Kolkata-700091, India

Corresponding Author(s) : Sumana Sengupta

sngsumana@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

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
Sengupta, S. ., Banerji, A. ., Prangé, T. ., Neuman, A. ., & Hazra, J. . (2020). [3+2] Cycloadditions: Part XXXV. Selective Cycloadditions of C-(4-Chlorophenyl)-N-methyl Nitrone to Cinnamic Acid Anilides. Asian Journal of Chemistry, 32(8), 1886–1894. https://doi.org/10.14233/ajchem.2020.22695
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