Synthesis of ۸-Aryl(alkyl)-۶-selenoxo-۶H-۱,۹-dioxa-۷-aza-cyclopenta[a]naphthalen-۳-ones Under Solvent-free Conditions at Ambient Temperature

۱,۳-Oxazine derivatives have found versatile applications as anti-bacterial and cancer-screening agents.۱They have antifungal action and are used as herbicides.۲,۳The thio derivatives of pyrano-۱,۳-benzoxazine have shown anti-inflammatory and antipyretic properties.۴Multi-component reactions (MCRs) are now frequently used by synthetic organic chemists as a facile means to generate molecular diversity from bifunctional substrates that react sequentially in an intramolecular fashion,۵and this approach may be used for the preparation of oxazines. There are several useful syntheses of oxazines,۶-۱۷ some of which were informed by a procedure first described by Khalilzadeh and co-workers۱۸who prepared a series of arylated bi- and tri-cyclic thioheterocycles via the N-methylimidazole-catalyzed reaction of phenol and ۱- and ۲-naphthols with acid chlorides and ammonium thiocyanate. This kindled our curiosity aboutthe cognate preparation of related selenium compounds. The current interest in selenium-containing organic compounds stems from their remarkable synthetic and biological functions.۱۹-۲۳The first synthesis of acyl isoselenocyanates, generated by the reaction of acyl chlorides and potassium selenocyanate, was described by Douglas.۲۴More recently, several preparations of heterocycles from acylhttp://chemistry.bcnf.ir Page ۲isoselenocyanates were reported.۲۵-۲۷In this context, we now describe a synthesis of novel۸-aryl(alkyl)-۶-selenoxo-۶H-۱,۹-dioxa-۷-aza-cyclopenta[a]naphthalen-۳-ones using themethod of Khalilzadeh.