35729-61-4Relevant academic research and scientific papers
Synthesis of new quinazoline-containing hydroxamic acids as potential HDAC/VEGFR inhibitors. Unusual rearrangements with pyrrolidone ring opening and dehydration of 3-N-hydroxyquinazoline fragment containing tetracycles
Kolotaev, Anton V.,Matevosyan, Karine R.,Osipov, Vasiliy N.,Khachatryan, Derenik S.
supporting information, (2019/11/28)
Synthesis pathways were developed and new hydroxamic acids were obtained as potential inhibitors of HDAC/VEGFR2, including tetracycles containing quinazolinone fragment as a “cap”. Further biological testing of the obtained compounds will give an opportunity to estimate the real prospects of the chosen research direction.
Reaction of anthranilic acid amides with cyclic anhydrides
Shemchuk,Chernykh,Krys'kiv
, p. 382 - 387 (2007/10/03)
Anthranilic acid amide reacts with cyclic anhydrides to give the corresponding N-acyl derivatives at the amino group, while analogous reactions of o-aminobenzohydroxamic acid lead to formation of 3-hydroxyquinazolin-4-ones under mild conditions. N-Acyl derivatives of anthranilic acid amide undergo intramolecular cyclization to imides on microwave irradiation or on melting, and their treatment with acetic anhydride in the presence of sodium acetate on heating yields quinazolin-4-ones. Pleiades Publishing, Inc., 2006.
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
