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Chemistry of 1,6‐diazaphenalene. Reaction with alkylating and acylating agents
Author(s) -
Avasthi Kamlakar,
Cook J. M.
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190632
Subject(s) - chemistry , alkylation , acylation , methyl iodide , imidazole , iodide , lithium iodide , reactivity (psychology) , halide , organic chemistry , bromide , lithium (medication) , ethyl iodide , medicinal chemistry , amide , catalysis , electrode , pathology , medicine , alternative medicine , electrolyte , endocrinology
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.