Abstract
AbstractA 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.
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