Article (Scientific journals)
An Unexpected Synthesis of Dihydrophenazines en Route to Benzimidazolium Salts
Borguet, Yannick; Zaragoza, Guillermo; Demonceau, Albert et al.
2012In Advanced Synthesis and Catalysis, 354 (7), p. 1356-1362
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Keywords :
electrocyclic reactions; ligand design; nitrogen heterocycles; oxidation; sigmatropic rearrangement
Abstract :
[en] The oxidation of various N,N′-diarylbenzene-1,2-diamines bearing bulky aromatic substituents with sodium periodate on wet silica gel afforded a series of five new dihydrophenazines instead of the expected cyclohexadiene-1,2-diimines. The reaction most likely proceeds via a 1,6-electrocyclic path and provides a convenient access to an important class of nitrogen heterocycles. Subsequent treatment of the mesityl derivative with chloromethyl pivalate and silver triflate led to the corresponding benzimidazolium salt.
Disciplines :
Chemistry
Author, co-author :
Borguet, Yannick ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Zaragoza, Guillermo
Demonceau, Albert ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Delaude, Lionel  ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
Language :
English
Title :
An Unexpected Synthesis of Dihydrophenazines en Route to Benzimidazolium Salts
Publication date :
2012
Journal title :
Advanced Synthesis and Catalysis
ISSN :
1615-4150
eISSN :
1615-4169
Publisher :
WILEY-VCH Verlag, Weinheim, Germany
Volume :
354
Issue :
7
Pages :
1356-1362
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 11 May 2012

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