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 Zur Forderung der Chemischen Wissenschaften
2018
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ir-20.500.12258-5392020-07-07T07:54:59Z Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2, 3-diones with cyclic ketazinones en route to spirocyclic scaffolds Rubin, M. A. Рубин, М. А. Nitrogen heterocycles Oxygen heterocycles Pyrrolediones Spiro compounds Synthetic methods 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 2018-06-08T12:58:15Z 2018-06-08T12:58:15Z 2017 Статья Dubovtsev, A.Yu., Dmitriev, M.V., Maslivets, A.N., Rubin, M. Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2, 3-diones with cyclic ketazinones en route to spirocyclic scaffolds // Beilstein Journal of Organic Chemistry. - 2017. - Volume 13. - pp. 2179-2185. https://www.scopus.com/record/display.uri?eid=2-s2.0-85033587113&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=nort*+caucas*+fed*+univ*&sid=d5d8a0d301244722be90437f5b553481&sot=afnl&sdt=cl&cluster=scopubyr%2c%222017%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=21&citeCnt=0&searchTerm= https://dspace.ncfu.ru:443/handle/20.500.12258/539 en Beilstein Journal of Organic Chemistry application/pdf application/pdf Beilstein-Institut Zur Forderung der Chemischen Wissenschaften |
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Nitrogen heterocycles Oxygen heterocycles Pyrrolediones Spiro compounds Synthetic methods |
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Nitrogen heterocycles Oxygen heterocycles Pyrrolediones Spiro compounds Synthetic methods Rubin, M. A. Рубин, М. А. Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2, 3-diones with cyclic ketazinones en route to spirocyclic scaffolds |
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 |
format |
Статья |
author |
Rubin, M. A. Рубин, М. А. |
author_facet |
Rubin, M. A. Рубин, М. А. |
author_sort |
Rubin, M. A. |
title |
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_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_sort |
regiodivergent condensation of 5-alkoxycarbonyl-1h-pyrrol-2, 3-diones with cyclic ketazinones en route to spirocyclic scaffolds |
publisher |
Beilstein-Institut Zur Forderung der Chemischen Wissenschaften |
publishDate |
2018 |
url |
https://www.scopus.com/record/display.uri?eid=2-s2.0-85033587113&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=nort*+caucas*+fed*+univ*&sid=d5d8a0d301244722be90437f5b553481&sot=afnl&sdt=cl&cluster=scopubyr%2c%222017%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=21&citeCnt=0&searchTerm= https://dspace.ncfu.ru:443/handle/20.500.12258/539 |
work_keys_str_mv |
AT rubinma regiodivergentcondensationof5alkoxycarbonyl1hpyrrol23dioneswithcyclicketazinonesenroutetospirocyclicscaffolds AT rubinma regiodivergentcondensationof5alkoxycarbonyl1hpyrrol23dioneswithcyclicketazinonesenroutetospirocyclicscaffolds |
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