Novel Synthesis of 1,4-Dialkoxy-5,6,7,8-multisubstituted-2,3-dicyanonaphthalenes through Electron Transfer from Mg Metal and Efficient Development of New Naphthalocyanines

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 se...

Full description

Saved in:
Bibliographic Details
Published inSynlett no. 6; pp. 862 - 868
Main Authors Miyazaki, Takeshi, Harada, Aiko, Maekawa, Hirofumi, Yamamoto, Yoshimasa, Nishiguchi, Ikuzo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
multisubstituted-2,3-dicyanonaphthalenes
benzyne
Mg metal naphthalocyanines
v(max) at 867-892 nm
DERIVATIVES
Online AccessGet more information

Cover

More Information
Summary: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 lambda(max) at 867-892 nm.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259910