synthesis of 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-n-methylethanamine via a [4+2] cycloaddition合成2 -(9 10-dihydro-9 10-propanoanthracen-9-yl)-n-methylethanamine通过[4 + 2]环加成作用.pdfVIP

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synthesis of 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-n-methylethanamine via a [4+2] cycloaddition合成2 -(9 10-dihydro-9 10-propanoanthracen-9-yl)-n-methylethanamine通过[4 + 2]环加成作用.pdf

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synthesisof2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-n-methylethanamineviaa[42]cycloaddition合成2-(910-dihydro-910-propanoanthracen-9-yl)-n-methylethanamine通过[42]环加成作用

Molecules 2010, 15, 4201-4206; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N- methylethanamine via a [4+2] Cycloaddition Usama Karama *, Adel Al-Saidey, Zeid Al-Othman and Abdel Rahman Almansour Department of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh - 11451, Saudi Arabia ∗ Author to whom correspondence should be addressed; E-Mail: karama@.sa; Fax: +9661-4675992. Received: 19 May 2010; in revised form: 31 May 2010 / Accepted: 1 June 2010 / Published: 9 June 2010 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 1. Introduction Benzoctamine [1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethanamine, 1, Figure 1] was synthesized and developed into a clinically useful drug for the treatment of anxiety by the Ciba-Geigy research group [1]. The key step was [4+2] cycloaddition of ethylene on 9-anthracenecarboxaldehyde