Convenient preparation of 1,2‐alkylenedioxy‐benzofuroxans and benzofurazans | Zendy

Takakis Ioannis M. | Zendy; Hadjimihalakis Phaedon M. | Zendy; Tsantali Georgia G. | Zendy; Pilini Helena | Zendy

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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 .

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