Synthesis and screening for antideperessant activity of some aminoindanooxazolines, aminoindanooxazines, and aminoacenaphthoxazolines

Abstract

Aminoindano and Related Compounds 3-(5-( 3-Acetamidophenyl)-2-tetrazolyl] propionic -2-tetrazolyl]propionic acid (7 g, 0.03 mol) was stirred for 12 hr at room temp in 100 ml of an equivolume mixture of AcaO-AcOH. The pale yellow ppt was reprecipitated from NaHCOs and recrystd from EtOH to give 5 g (61%) of pale yellow crystals, mp 207°.3-[5-(3-Phenylazophenyl)-2-tetrazolyl]propionic Acid (30).-To a solution of 7 g (0.03 mol) of 3-[5-(3-aminophenyl)-2-tetrazolyl]propionic acid in 75 ml of glacial AcOH was added 3.25 g (0.03 mol) of nitrosobenzene. After stirring at room temp for 16 hrs the ppt was collected and dried. Two recrvstallizations from aq MeOH gave 5 g (52%) of red crystals, mp 155°.3-(5-Phenyl-l-tetrazolyl)propionic Acid (44).-PC15 (51 g, 0.245 mol) was added portionwise to a solution of ethyl 3benzamidopropionate (50 g, 0.232 mol) in 300 ml of dry CeH6. The solution was refluxed until the evolution of HC1 ceased. After cooling, 100 g of a 13.4% solution of HN3 in CeHe17 was added. After stirring for 1 hr at 0°and 16 hr at reflux, HC1 gas ceased to evolve. The solvent was removed under recuced pres-(17) J. von Braun, Justus Liebigs Ann. Chem., 490, 100 (1931).