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Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
Yu, Alexey Dmitriev, Maksim V. Maslivets, Andrey N. Rubin, Michael
Yu, Alexey
Dmitriev, Maksim V.
Maslivets, Andrey N.
Rubin, Michael
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Abstract
The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane. The control of this regioselectivity is efficiently governed by steric effects at the hydrazone moiety of the ketazinone reagent.
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Date
2017-10-19
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Beilstein
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Keywords
Nitrogen heterocycles, Pyrrolediones, Spiro compounds, Synthetic methods, Oxygen heterocycles
Citation
Dubovtsev, A. Y.; Dmitriev, M. V.; Maslivets, А. N.; Rubin, M. Beilstein Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds. J. Org. Chem. 2017, 13, 2179–2185. doi:10.3762/bjoc.13.218