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Iron(III)-catalyzed selective N–O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from N-vinyl-α,β-unsaturated ketonitrones

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Abstract

An iron(III)-catalyst controlled cyclization and selective N–O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(II) acetate in combination with the prepared bidentate N-ligand was used.

Graphical abstract: Iron(iii)-catalyzed selective N–O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from N-vinyl-α,β-unsaturated ketonitrones

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Publication details

The article was received on 25 Feb 2018, accepted on 05 May 2018 and first published on 08 May 2018


Article type: Paper
DOI: 10.1039/C8GC00630J
Citation: Green Chem., 2018, Advance Article
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    Iron(III)-catalyzed selective N–O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from N-vinyl-α,β-unsaturated ketonitrones

    C. Chen, Q. Wu, C. Wei, C. Liang, G. Su and D. Mo, Green Chem., 2018, Advance Article , DOI: 10.1039/C8GC00630J

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