(4+3) cycloaddition reactions in organic synthesis: Synthesis of Bishomomaprotiline [9,10-dihydro-9-(4-methylaminobutyl)-9,10- propanoanthracene]

Adel Al-Saeedi, Usama Karama,

Abstract

The reactions between oxyallyl cations and 9-substituted anthracene to obtain 9,10-dihydro-9,10- propanoanthracene substituted have not yet been studied extensively. For this reason, we used (4+3) cycloaddition reactions of 9-(4-pentenyl)-anthracene with 1,1,3,3-tetrabromoacetone as key step for preparation of a homologue of maprotiline which has been synthesized and developed into a clinically useful drug for the treatment of depressant by Ciba-Geigy research group in Switzerland.