Synthesis of 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-N-methylethanaminevia a [4+2] cycloaddition

Usama Karama; Adel Al-Saidey; Zeid Al-Othman; Abdel Rahman Almansour

doi:10.3390/molecules15064201

Synthesis of 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-N-methylethanaminevia a [4+2] cycloaddition

Molecules. 2010 Jun 9;15(6):4201-6. doi: 10.3390/molecules15064201.

Authors

Usama Karama¹, Adel Al-Saidey, Zeid Al-Othman, Abdel Rahman Almansour

Affiliation

¹ Department of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh-11451, Saudi Arabia. karama@ksu.edu.sa

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 alpha-bromoacrolein and 9-allyl-anthracene, followed by ring expansion and samarium diiodide deoxygenation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthracenes / chemistry*
Antidepressive Agents / chemical synthesis*
Antidepressive Agents / chemistry
Molecular Structure

Substances

Anthracenes
Antidepressive Agents
benzoctamine