[3+2] Cycloadditions: Part XXXIV: Further Investigations of Cycloadditions of C,N-Diaryl- and C-Aryl-N-methyl Nitrones to α,β-Unsaturated Esters

Sumana Sengupta1,2,* and Avijit Banerji1,3

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

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

Abstract

Investigations of [3+2] cycloadditions of C,N-diaryl and C-aryl-N-methyl nitrones as three atom components (TAC) to substituted methyl E-cinnamates and diethyl arylidene malonates have been further investigated. [3+2] Cycloadditions of cinnamates yielded mixtures of cycloadducts, the major products being the 3,4-trans-4,5-trans-2,3,5-triaryl-4-carbomethoxy products originating from the endo-carbonyl-exo-aryl meta channel approach of the cinnamate component. [3+2] Cycloadditions to diethyl arylidene malonates furnished single cycloadducts-3,5-trans-2-methyl-3,5-diaryl-4,4- dicarbethoxy isoxazolidines by a endo-aryl meta channel approach of the 2π-component.

Keywords

[3+2] Cycloadditions, Methyl E-Cinnamate, Diarylidene malonate, Nitrone, Isoxazolidine, XRD.

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