140472-37-3Relevant academic research and scientific papers
Electrochemical reduction of N-(o-nitrobenzoyl) and N-(o-nitrobenzyl)-amides or imides. Electrosynthesis of quinazoline derivatives.
Chibani, A.,Hazard, R.,Tallec, A.
, p. 814 - 822 (2007/10/02)
Controlled potential electrolysis at a mercury pool cathode, carried out at the plateau of the first reduction wave of o-nitrobenzoylacetamide, leads to 4-hydroxy-2-methylquinazoline 1-oxide, resulting from a ring closure of the phenylhydroxylamine intermediate.In the same conditions, o-nitrobenzoylsuccinimide gives rise to a tricyclic compound which undergoes a nucleophilic attack from the electrolysis medium, with formation of 4-hydroxyquinazoline 1-oxide bearing at the position 2, either a propanoate group (acidic media) or a propanamido group (ammoniacal buffer).At last, the hydroxylamino derivative issued from o-nitrobenzoyl- phtalimide reduction, disproportionates in acidic medium and a mixture of 2-(o-carboxyphenyl)-4-hydroxyquinazoline 1-oxide and of the parent quinazoline is obtained at the term of the electrolysis.As a matter of comparison, the parent o-nitrobenzyl substrates have been studied; no ring closure occurs at the hydroxylamino stage but quinazoline derivatives can be obtained from the corresponding anilines by electroreduction at more negative potentials. Key words: polarography / cyclic voltammetry / controlled potential electrolysis / quinazoline 1-oxyde / quinazoline
