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Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative Cyclization Reactions
[Image: see text] A flexible synthesis of dibenzo[e,g]isoindol-1-ones has been developed. Dibenzo[e,g]isoindol-1-ones represent simplified benzenoid analogues of biological indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-ones (indolocarbazoles), compounds that have demonstrated a wide range of biological acti...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156242/ https://www.ncbi.nlm.nih.gov/pubmed/25138638 http://dx.doi.org/10.1021/jo501185f |
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author | van Loon, Amy A. Holton, Maeve K. Downey, Catherine R. White, Taryn M. Rolph, Carly E. Bruening, Stephen R. Li, Guanqun Delaney, Katherine M. Pelkey, Sarah J. Pelkey, Erin T. |
author_facet | van Loon, Amy A. Holton, Maeve K. Downey, Catherine R. White, Taryn M. Rolph, Carly E. Bruening, Stephen R. Li, Guanqun Delaney, Katherine M. Pelkey, Sarah J. Pelkey, Erin T. |
author_sort | van Loon, Amy A. |
collection | PubMed |
description | [Image: see text] A flexible synthesis of dibenzo[e,g]isoindol-1-ones has been developed. Dibenzo[e,g]isoindol-1-ones represent simplified benzenoid analogues of biological indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-ones (indolocarbazoles), compounds that have demonstrated a wide range of biological activity. The synthesis of the title compounds involved tetramic acid sulfonates. Different aryl groups were introduced at C4 of the heterocyclic ring via Suzuki–Miyaura cross-coupling reactions. Finally, mild Scholl-type oxidative cyclizations mediated by phenyliodine(III) bis(trifluoroacetate) (PIFA) converted some of the latter compounds into the corresponding dibenzo[e,g]isoindol-1-ones. A systematic study of the oxidative cyclization revealed the following reactivity trend: 3,4-dimethoxyphenyl ≫ 3-methoxyphenyl > 3,4,5-trimethoxyphenyl > 4-methoxyphenyl ≈ phenyl. Overall, the oxidative cyclization required at least two methoxy groups distributed in the aromatic rings, at least one of which had to be located para to the site of the cyclization. |
format | Online Article Text |
id | pubmed-4156242 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41562422015-08-19 Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative Cyclization Reactions van Loon, Amy A. Holton, Maeve K. Downey, Catherine R. White, Taryn M. Rolph, Carly E. Bruening, Stephen R. Li, Guanqun Delaney, Katherine M. Pelkey, Sarah J. Pelkey, Erin T. J Org Chem [Image: see text] A flexible synthesis of dibenzo[e,g]isoindol-1-ones has been developed. Dibenzo[e,g]isoindol-1-ones represent simplified benzenoid analogues of biological indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-ones (indolocarbazoles), compounds that have demonstrated a wide range of biological activity. The synthesis of the title compounds involved tetramic acid sulfonates. Different aryl groups were introduced at C4 of the heterocyclic ring via Suzuki–Miyaura cross-coupling reactions. Finally, mild Scholl-type oxidative cyclizations mediated by phenyliodine(III) bis(trifluoroacetate) (PIFA) converted some of the latter compounds into the corresponding dibenzo[e,g]isoindol-1-ones. A systematic study of the oxidative cyclization revealed the following reactivity trend: 3,4-dimethoxyphenyl ≫ 3-methoxyphenyl > 3,4,5-trimethoxyphenyl > 4-methoxyphenyl ≈ phenyl. Overall, the oxidative cyclization required at least two methoxy groups distributed in the aromatic rings, at least one of which had to be located para to the site of the cyclization. American Chemical Society 2014-08-19 2014-09-05 /pmc/articles/PMC4156242/ /pubmed/25138638 http://dx.doi.org/10.1021/jo501185f Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | van Loon, Amy A. Holton, Maeve K. Downey, Catherine R. White, Taryn M. Rolph, Carly E. Bruening, Stephen R. Li, Guanqun Delaney, Katherine M. Pelkey, Sarah J. Pelkey, Erin T. Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative Cyclization Reactions |
title | Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative
Cyclization
Reactions |
title_full | Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative
Cyclization
Reactions |
title_fullStr | Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative
Cyclization
Reactions |
title_full_unstemmed | Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative
Cyclization
Reactions |
title_short | Preparation of Dibenzo[e,g]isoindol-1-ones via Scholl-Type Oxidative
Cyclization
Reactions |
title_sort | preparation of dibenzo[e,g]isoindol-1-ones via scholl-type oxidative
cyclization
reactions |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156242/ https://www.ncbi.nlm.nih.gov/pubmed/25138638 http://dx.doi.org/10.1021/jo501185f |
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