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Synthesis of dimethoxy‐ and dioxano‐annellated benzofuroxans from o ‐dinitroarenes
Author(s) -
Eswaran S. V.,
Sajadian S. K.
Publication year - 1988
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.5570250319
Subject(s) - chemistry , furoxan , sodium azide , azide , nucleophilic substitution , ring (chemistry) , thermal decomposition , nucleophile , pyrolytic carbon , medicinal chemistry , nitro , combinatorial chemistry , stereochemistry , organic chemistry , pyrolysis , alkyl , nitric oxide , catalysis
Abstract Thermolysis of 4,5‐dinitroveratrole 1a in the presence of sodium azide and dimethylsulfoxide gives the new 5,6‐dimethoxybenzofuroxan, 2a , whereas 3,4,5‐trinitroveratrole led to the new 5(7),6‐dimethoxy‐4‐nitrobenzofuroxans 2e, 3e via a nucleophilic substitution of a nitro group by azide ion and pyrolytic ring closure. This method provides a simpler route to the known 1,3‐benzodioxano[5,6‐ c ]furoxan, 2b and 1,4‐benzodioxano[6,7‐ c ]furoxan 2c , as well.