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

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....

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Main Authors: Alexey Yu. Dubovtsev, Maksim V. Dmitriev, Аndrey N. Maslivets, Michael Rubin
Format: Article
Language:English
Published: Beilstein-Institut 2017-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.13.218
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author Alexey Yu. Dubovtsev
Maksim V. Dmitriev
Аndrey N. Maslivets
Michael Rubin
author_facet Alexey Yu. Dubovtsev
Maksim V. Dmitriev
Аndrey N. Maslivets
Michael Rubin
author_sort Alexey Yu. Dubovtsev
collection DOAJ
description 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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spelling doaj.art-894c0a7bae6345e9bb3859bd58519ad22022-12-21T20:01:43ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-10-011312179218510.3762/bjoc.13.2181860-5397-13-218Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffoldsAlexey Yu. Dubovtsev0Maksim V. Dmitriev1Аndrey N. Maslivets2Michael Rubin3Department of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian FederationDepartment of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian FederationDepartment of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian FederationDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian FederationThe 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.https://doi.org/10.3762/bjoc.13.218nitrogen heterocyclesoxygen heterocyclespyrroledionesspiro compoundssynthetic methods
spellingShingle Alexey Yu. Dubovtsev
Maksim V. Dmitriev
Аndrey N. Maslivets
Michael Rubin
Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
Beilstein Journal of Organic Chemistry
nitrogen heterocycles
oxygen heterocycles
pyrrolediones
spiro compounds
synthetic methods
title Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_full Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_fullStr Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_full_unstemmed Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_short Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_sort regiodivergent condensation of 5 alkoxycarbonyl 1h pyrrol 2 3 diones with cyclic ketazinones en route to spirocyclic scaffolds
topic nitrogen heterocycles
oxygen heterocycles
pyrrolediones
spiro compounds
synthetic methods
url https://doi.org/10.3762/bjoc.13.218
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