Synthesis of dimethoxy‐ and dioxano‐annellated benzofuroxans from  o ‐dinitroarenes | Zendy

Eswaran S. V. | Zendy; Sajadian S. K. | Zendy

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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

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.

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