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Molecules 2010, 15(6), 4201-4206; doi:10.3390/molecules15064201

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

Department of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh - 11451, Saudi Arabia
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Received: 19 May 2010 / Revised: 31 May 2010 / Accepted: 1 June 2010 / Published: 9 June 2010
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Abstract

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.
Keywords: benzoctamine; homologue; antidepressant; ring expansion; cycloaddition benzoctamine; homologue; antidepressant; ring expansion; cycloaddition
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Karama, U.; Al-Saidey, A.; Al-Othman, Z.; Almansour, A.R. Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition. Molecules 2010, 15, 4201-4206.

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