Azaloxan

Azaloxan is a drug which was patented as an antidepressant by Ciba-Geigy in the early 1980s, but was never marketed.

Synthesis

Thymoleptic described as a “psychostimulant” according to patent title.
The halogenation of allyl cyanide with bromine gives 3,4-dibromobutyronitrile . This is further reacted with catechol to give the 1,4-benzodioxan-2-yl-acetonitrile . Acid catalyzed hydrolysis of the nitrile to the acid gives 1,4-benzodioxan-2-yl-acetic acid . The reduction of this to alcohol with sodium bis(2-methoxyethoxy)aluminium hydride gives 2-ethanol . The tosylation of this intermediate gives . The synthesis concludes with an SN-2 displacement reaction with 1--2-imidazolidinone completing the synthesis of .