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Convenient preparation of 1,2‐alkylenedioxy‐benzofuroxans and benzofurazans
Author(s) -
Takakis Ioannis M.,
Hadjimihalakis Phaedon M.,
Tsantali Georgia G.,
Pilini Helena
Publication year - 1992
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.5570290122
Subject(s) - chemistry , triphenylphosphine , deoxygenation , nitration , azide , nucleophilic substitution , thermal decomposition , medicinal chemistry , nucleophile , decomposition , ion , organic chemistry , pyrolysis , catalysis
Nitration of the dioxolo‐annelated benzenes 11 led to the corresponding dinitro derivatives 12 . Nucleophilic substitution of the latter with azide ion furnished the monoazides 13 which on thermolysis afforded the benzofuroxans 14 . Deoxygenation of furoxans 1a,b,e,f, 2a‐c,e,f, 5, 7, 9 and 14 with triphenylphosphine, furnished the respective benzofurazans 3a,b,e,f, 4a‐c,e,f, 6, 8, 10 and 15 .