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Synthesis and reactivity of a series of [14]azaannulenes
Author(s) -
Place David A.,
Ferrara Gerald P.,
Harland Joseph J.,
Dabrowiak James C.
Publication year - 1980
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.5570170305
Subject(s) - chemistry , steric effects , reagent , reactivity (psychology) , nucleophile , diketone , nickel , diamine , series (stratigraphy) , medicinal chemistry , organic chemistry , catalysis , medicine , paleontology , alternative medicine , pathology , biology
Using a metal template reaction, a series of [14]azaannulenes formed from a β‐diketone and an aromatic diamine in the presence of nickel(II) have been synthesized. Attempted cyclizations with bulky β‐diketones and certain substituted diamines showed that the cyclization is sensitive to steric effects. At least one of the nickel complexes readily reacts with a series of nucleophilic reagents to give methine‐substituted products.