Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition

The synthesis of the tetracyclic molecule 2-(9,10-dihydro-9,10-propano-anthracen-9-yl)-N-methylethanamine (2) as a homologue of the antidepressant 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethaneamine (1) was described. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthr...

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Autores principales: Karama, Usama, Al-Saidey, Adel, Al-Othman, Zeid, Almansour, Abdel Rahman
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264365/
https://www.ncbi.nlm.nih.gov/pubmed/20657434
http://dx.doi.org/10.3390/molecules15064201
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author Karama, Usama
Al-Saidey, Adel
Al-Othman, Zeid
Almansour, Abdel Rahman
author_facet Karama, Usama
Al-Saidey, Adel
Al-Othman, Zeid
Almansour, Abdel Rahman
author_sort Karama, Usama
collection PubMed
description The synthesis of the tetracyclic molecule 2-(9,10-dihydro-9,10-propano-anthracen-9-yl)-N-methylethanamine (2) as a homologue of the antidepressant 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethaneamine (1) was described. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one (7) was successfully synthesized via a [4+2] cycloaddition of α-bromoacrolein and 9-allyl-anthracene, followed by ring expansion and samarium diiodide deoxygenation.
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spelling pubmed-62643652018-12-04 Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition Karama, Usama Al-Saidey, Adel Al-Othman, Zeid Almansour, Abdel Rahman Molecules Article The synthesis of the tetracyclic molecule 2-(9,10-dihydro-9,10-propano-anthracen-9-yl)-N-methylethanamine (2) as a homologue of the antidepressant 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethaneamine (1) was described. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one (7) was successfully synthesized via a [4+2] cycloaddition of α-bromoacrolein and 9-allyl-anthracene, followed by ring expansion and samarium diiodide deoxygenation. MDPI 2010-06-09 /pmc/articles/PMC6264365/ /pubmed/20657434 http://dx.doi.org/10.3390/molecules15064201 Text en © 2010 by the authors; licensee MDPI, Basel, Switzerland. This article is an Open Access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Karama, Usama
Al-Saidey, Adel
Al-Othman, Zeid
Almansour, Abdel Rahman
Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition
title Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition
title_full Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition
title_fullStr Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition
title_full_unstemmed Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition
title_short Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition
title_sort synthesis of 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-n-methylethanamine via a [4+2] cycloaddition
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264365/
https://www.ncbi.nlm.nih.gov/pubmed/20657434
http://dx.doi.org/10.3390/molecules15064201
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