New routes condensed polynuclear compounds.

Aza-ortho-xylylenes in Organic Synthesis

“…[31] The formation of benzoazetines is suppressed by a competitive addition of amide anion to the intermediate aryne, [31] or by a ring-closure of an ambident aniline anion, producing phenanthridines. [32] Beak et al obtained N-acetylbenzoazetine (32) in an intramolecular reaction of N-methoxy-2-bromobenzylamine (31), doubly lithiated with methyllithium and tert-butyllithium (Scheme 7). [33] No attempts to apply 32 as an azaortho-xylylene precursor were undertaken.…”