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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Beilstein-Institut
2017-10-01
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Series: | Beilstein Journal of Organic Chemistry |
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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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id | doaj.art-894c0a7bae6345e9bb3859bd58519ad2 |
institution | Directory Open Access Journal |
issn | 1860-5397 |
language | English |
last_indexed | 2024-12-19T23:31:01Z |
publishDate | 2017-10-01 |
publisher | Beilstein-Institut |
record_format | Article |
series | Beilstein Journal of Organic Chemistry |
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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