Chemistry of 1,6-diazaphenalene. Reaction with alkylating and acylating agents

A study of the reactivity of 1,6-diazaphenalene ( 1 ) toward alkylating and acylating agents has been carried out in order to investigate the chemistry of this new heterocycle. Attempts to alkylate 1 were successfully completed by stirring the lithium stabilized anion of 1 with either methyl iodide or benzyl bromide to provide N-alkyldiazaphenalenes 4 and 5, respectively, whereas, experiments performed to alkylate 1 under conditions employed for alkylation of imidazole were unsuccessful. Studies directed toward acylation of 1 did not lead, in general, to isolable acyldiazaphenalenes; however, in one specific case successful acylation of 2-chloro-9-methoxy-1,6-diazaphenalene ( 10 ) did provide a characterisable amide ( 14 ). Where possible the chemistry of 1,6-diazaphenalene has been compared to that reported for imidazole.