Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/54401
Title: [3+2] Cycloadditions. Part XXXIII. Selective cycloadditions of C-(1-naphthyl)-N-methyl nitrone and C-phenyl-N-benzyl nitrone to α,β-unsaturated carbonyl compounds1,2
Authors: Banerji, Avijit
Ghosh, Anindita
Banerji, Julie
Prangé, Thierry
Rao, Mruthyumjaya Meda
Keywords: Nitrones;Cycloadditions;Isoxazolidines;XRD;DFT
Issue Date: Apr-2020
Publisher: NISCAIR-CSIR, India
Abstract: [3+2] Cycloadditions [32CA] involving nitrones as 1,3-dipolar species to alkenes yield isoxazolidines, which on further transformations can be converted to naturally occurring bioactive compounds. Thus the 32CA route provides conversion of simple natural products to more complex natural occurring bioactive nitrogen heterocycles, and close analogues. The present work deals with 32CA between the nitrones C-(1-naphthyl)-N-methyl nitrone and C-phenyl-N-benzyl nitrone to
α,β-unsaturated carbonyl compounds as dipolarophiles, viz. arylidene malonate esters, methyl cinnamate and benzylidene acetophenone (chalcone). Methyl cinnamate is a naturally occurring compound, while the chalcone scaffold is present in several natural products. Structure elucidation of the generated cycloadducts have been achieved by means of detailed spectroscopic and XRD studies. All the cycloadditions investigated occurr regioselectively to yield tetra/penta-substituted isoxazolidines, where the carbonyl group(s) are situated at the 4-position of the isoxazolidine ring. DFT computations including optimised geometries, FMO energies, electronic chemical potentials, chemical hardness, chemical softness and reactivity indices of a number of the reactants have been calculated at DFT/B3LYP/6-31++G(d,p) level of theory. The calculated reactivity indices have been used to analyse the 32CAs studied and to predict the regioselectivities; the predictions are in excellent accord with the experimental results.
Page(s): 488-501
URI: http://nopr.niscair.res.in/handle/123456789/54401
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.59B(04) [April 2020]

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IJCB 59B(4) 488-501_Suppl Data 2.pdfSupplementary Data 2230.12 kBAdobe PDFView/Open
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