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Facile access to organotellurium heterocycles by nitration of bis(3,5‐dimethylphenyl) ditelluride
Author(s) -
Mallikarachy Prabodhika R.,
Brotherton Harry O.,
Fronczek Frank R.,
Junk Thomas
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420210
Subject(s) - nitration , chemistry , tellurium , medicinal chemistry , nitrogen , organic chemistry
Efficient access to bis(nitrophenyl) ditellurides was developed and their utility for the preparation of novel nitrogen‐containing organotellurium heterocycles demonstrated. The nitration of diphenyl ditellurides resulted in their oxidation to benzenetellurinic acids, followed by nitration in ortho or meta positions relative to tellurium. Nitration of bis(3,5‐dimethylphenyl) ditelluride furnished bis(3,5‐dimethyl‐2‐nitrophenyl) ditelluride, which was elaborated into 2,4,6‐trimethylbenzotellurazole and ( Z )‐2‐methoxycarbonylmethylene‐3,4‐dihydro‐3‐oxo‐2 H ‐benzo‐1,4‐tellurazine, the first reported 3,4‐dihydro‐2 H ‐benzo‐1,4‐tellurazine. This compound, as well as 2,4,6‐trimethyltellurazolium (4‐dicyanomethylene‐cyclohexa‐2,5‐dienylidene)cyanoacetate were characterized by x‐ray crystallography.