Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis
ß-Oxo-1 and 9-anthracenepropionate (6 and 7) reacts with DMF-acetale to enaminones 10 and 11. The reaction of 2-(dimethylamino)methylen-substituted ß-oxo-1 -anthracenepropionate (10) with hydrazines yields 5-(l-anthracenyl)-pyrazol-4-carboxylates (13). In contrast, the cyclocondensation of 3-(9-anth...
Published in: | Zeitschrift für Naturforschung B |
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Walter de Gruyter GmbH
1999
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crdegruyter:10.1515/znb-1999-0908 2024-06-23T07:52:03+00:00 Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis Knieß, Astrid Gruner, Margit Mayer, Roland 1999 http://dx.doi.org/10.1515/znb-1999-0908 https://www.degruyter.com/view/journals/znb/54/9/article-p1133.xml https://www.degruyter.com/document/doi/10.1515/znb-1999-0908/xml https://www.degruyter.com/document/doi/10.1515/znb-1999-0908/pdf en eng Walter de Gruyter GmbH Zeitschrift für Naturforschung B volume 54, issue 9, page 1133-1137 ISSN 1865-7117 0932-0776 journal-article 1999 crdegruyter https://doi.org/10.1515/znb-1999-0908 2024-06-04T05:48:40Z ß-Oxo-1 and 9-anthracenepropionate (6 and 7) reacts with DMF-acetale to enaminones 10 and 11. The reaction of 2-(dimethylamino)methylen-substituted ß-oxo-1 -anthracenepropionate (10) with hydrazines yields 5-(l-anthracenyl)-pyrazol-4-carboxylates (13). In contrast, the cyclocondensation of 3-(9-anthracenyl)-2-(dimethylamino)methylen-3-oxo-propionate (11) with hydrazine hydrochlorides gives 4-(9-anthracenoyl)-5-hydroxy-pyrazoles (14). This is caused by the sterical hindrance of the carbonyl group of the anthracene derivatives in position 9; thus, the cyclocondensation proceeds via reaction of the ester group of the enaminone 11. Article in Journal/Newspaper Carbonic acid De Gruyter Zeitschrift für Naturforschung B 54 9 1133 1137 |
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Open Polar |
collection |
De Gruyter |
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crdegruyter |
language |
English |
description |
ß-Oxo-1 and 9-anthracenepropionate (6 and 7) reacts with DMF-acetale to enaminones 10 and 11. The reaction of 2-(dimethylamino)methylen-substituted ß-oxo-1 -anthracenepropionate (10) with hydrazines yields 5-(l-anthracenyl)-pyrazol-4-carboxylates (13). In contrast, the cyclocondensation of 3-(9-anthracenyl)-2-(dimethylamino)methylen-3-oxo-propionate (11) with hydrazine hydrochlorides gives 4-(9-anthracenoyl)-5-hydroxy-pyrazoles (14). This is caused by the sterical hindrance of the carbonyl group of the anthracene derivatives in position 9; thus, the cyclocondensation proceeds via reaction of the ester group of the enaminone 11. |
format |
Article in Journal/Newspaper |
author |
Knieß, Astrid Gruner, Margit Mayer, Roland |
spellingShingle |
Knieß, Astrid Gruner, Margit Mayer, Roland Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis |
author_facet |
Knieß, Astrid Gruner, Margit Mayer, Roland |
author_sort |
Knieß, Astrid |
title |
Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis |
title_short |
Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis |
title_full |
Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis |
title_fullStr |
Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis |
title_full_unstemmed |
Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis |
title_sort |
reaktionsverhalten von β-oxo-carbonsäurederivaten der anthracenreihe bei der synthese von pyrazolen / on the reaction behavior of ß-oxo carbonic acid derivatives of the anthracene series in pyrazole synthesis |
publisher |
Walter de Gruyter GmbH |
publishDate |
1999 |
url |
http://dx.doi.org/10.1515/znb-1999-0908 https://www.degruyter.com/view/journals/znb/54/9/article-p1133.xml https://www.degruyter.com/document/doi/10.1515/znb-1999-0908/xml https://www.degruyter.com/document/doi/10.1515/znb-1999-0908/pdf |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
Zeitschrift für Naturforschung B volume 54, issue 9, page 1133-1137 ISSN 1865-7117 0932-0776 |
op_doi |
https://doi.org/10.1515/znb-1999-0908 |
container_title |
Zeitschrift für Naturforschung B |
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54 |
container_issue |
9 |
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1133 |
op_container_end_page |
1137 |
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1802643245937721344 |