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Transformations on 2,3,4,5‐tetrahydrobenzo[ b ][1,4]‐dioxocin leading to substituted ortho ‐nitroaryl azides, benzofuroxans, benzofurazans and related compounds
Author(s) -
Takakis Ioannis M.,
Hadjimihalakis Phaedon M.
Publication year - 1991
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.5570280533
Subject(s) - chemistry , nitration , thermal decomposition , electrophilic aromatic substitution , electrophile , hydrolysis , medicinal chemistry , nucleophilic substitution , electrophilic substitution , nucleophile , decomposition , organic chemistry , catalysis
Nitration of the acetamido‐nitrobenzodioxocins 10 , prepared from the corresponding amino derivatives 9 , led to the acetamido‐dinitrobenzodioxocins 11 , hydrolysis of which furnished the corresponding amines 13 . Preparation of the dinitroazides 18 and acetamido‐nitroazides 21 as precursors to substituted dioxocino‐annelated benzofuroxans is described. Thermolysis of the dinitro‐azido derivatives 18a,c,e and/or direct nitration of the unsubstituted benzofuroxans 1a, 2a afforded the isomeric nitrobenzofuroxans 1b, 2b,c . Thermolysis of the acetamido‐nitroazides 21 gave the acetamidobenzofuroxans 1d, 2d,e . All benzofuroxans were deoxygenated to the corresponding benzofurazans 3b,d, 4b‐e . Some aspects of electrophilic and nucleophilic aromatic substitution are discussed.