Synthesis of 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-N-methylethanaminevia 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-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.
Karama
Usama
U
Department of Chemistry, College of Science, King Saud University, P.O.Box 2455, Riyadh-11451, Saudi Arabia. karama@ksu.edu.sa
Al-Saidey
Adel
A
Al-Othman
Zeid
Z
Almansour
Abdel Rahman
AR
D000873:Anthracenes / Q000737:chemistry*; D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000873:Anthracenes; D000928:Antidepressive Agents; C100247:benzoctamine