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Synthesis of 4‐amino[1] benzofuro[3,2‐ g ] cinnolines
Author(s) -
Ladurée D.,
Florentin D.,
Robba M.
Publication year - 1980
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.5570170607
Subject(s) - chemistry , dibenzofuran , intramolecular force , salt (chemistry) , condensation , methylene , stereochemistry , medicinal chemistry , organic chemistry , physics , thermodynamics
The synthesis of the new heterocycles, 4‐amino[1]benzofuro[3,2‐ g ]cinnolines, was accomplished by the intramolecular cyclization of the Z ‐configuration of cyanoarylhydrazones. The latter compounds were obtained via interaction between the diazonium salt of 3‐amino‐dibenzofuran and various active methylene compounds via the Japp‐Klingemann reaction. The alkaline treatment of azo intermediates 4 , which may be isolated in the course of condensation, gave the corresponding cyanoarylhydrazones 5 . A study of the configuration and possible isomerisations is reported.