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An Unexpected Synthesis of Dihydrophenazines en Route to Benzimidazolium Salts
Author(s) -
Borguet Yannick,
Zaragoza Guillermo,
Demonceau Albert,
Delaude Lionel
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100890
Subject(s) - chemistry , sodium periodate , trifluoromethanesulfonate , salt (chemistry) , periodate , sodium salt , derivative (finance) , polymer chemistry , organic chemistry , medicinal chemistry , catalysis , inorganic chemistry , financial economics , economics
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.