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Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds.

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.

SUBMITTER: Dubovtsev AY

PROVIDER: S-EPMC5669231 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Regiodivergent condensation of 5-alkoxycarbonyl-1<i>H</i>-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds.

Dubovtsev Alexey Yu AY Dmitriev Maksim V MV Maslivets Аndrey N АN Rubin Michael M

Beilstein journal of organic chemistry 20171019

The condensation of 5-alkoxycarbonyl-1<i>H</i>-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. ...[more]

PMID: 29114325

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