Abstract
Novel methods for efficient synthesis of 1,4-diamyloxy-5,6,7,8-multisubstituted-2,3-dicyanonaphthalenes
were successfully developed, starting from easily available 2,3-dicyanohydroquinone
as a common single compound through only three steps, the first
dibromination of 2,3-dicyanohydroquinone, the second Mitsunobu dialkylation
of 2,3-dicyano-5,6-diboromo-1,4-hydroquinone, and the last Diels-Alder-type
of cycloaddition between 1,4-alkoxy-2,3-dicyano-5,6-diboromobenzenes
and multisubstituted furans, followed by reductive deoxygenation
with Mg turning. The obtained 1,4-diamyloxy-5,6,7,8-multisubstituted-2,3-dicyanonaphthalenes
were easily transformed into the corresponding naphthalocyanines
in 20-45% yields which showed their λmax at 867-892
nm.
Key words
multisubstituted-2,3-dicyanonaphthalenes - Mg metal naphthalocyanines - benzyne - νmax at 867-892
nm
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