An Unexpected Synthesis of Dihydrophenazines en Route to Benzimidazolium Salts

[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 :

Pages :

1356-1362

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 11 May 2012

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