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Publikācija: A Novel Route to 3-Aryl-2-Styrylquinazolin-4(3H)-Ones

Publication Type Conference paper
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language A Novel Route to 3-Aryl-2-Styrylquinazolin-4(3H)-Ones
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Inese Mieriņa
Māra Jure
Abstract Compounds containing 3-aryl-2-styrylquinazolin-4(3H)-one1 moiety demonstrate wide range of biological activity – e.g., an antibiotic effect in vivo against methicillin-resistant Staphylococcus aureus1and antileishmanial2and anticancer activity.3 Usually these compounds are obtained from 2- methylbenz[1,3]oxazin-2-ones by cleavage with aromatic amines and following aldol condensation. Unfortunately, when this reaction is realized with 2-styrylbenz[1,3]oxazin-2-ones 2, a mixture of quinazolinones 1 and 2-acylamino-N-benzamides 3 is obtained. Herein, we present a novel method for synthesis of 3-aryl-2-styrylquinazolin-4(3H)-ones 1 starting from 2-styrylbenzoxazinones 2 and aromatic amines, followed by intramolecular cyclization. Intermediates 3 were obtained by heating of heterocycles 2 and anilinesin inert solvent: when the reaction was realized with sterically hindered anilines or aromatic amines containing electronwithdrawing groups, dianilides 3 were formed exclusively with good yields by heating in xylenes. In other cases the mixture of dianilide 3 and quinazolinone 1 was obtained or even the last one formed as the only product. It was found out that the cyclization of compounds 3 can be successfully realized by treatment with HMDS and TMS-Cl in presence of in situ generated iodine. Such reaction could proceed via silylation followed by in situ ring closure and deoxysilylation. Till now, similar reactions have been described only for dianilides of anthranilic acid, which do not contain styryl substituent.4Antiradical activity of the synthesized compounds 1 and 3 was studied.
Hyperlink: http://www.innovabalt.eu/pictures/zinas/225.pdf 
Reference Mieriņa, I., Jure, M. A Novel Route to 3-Aryl-2-Styrylquinazolin-4(3H)-Ones. In: Drug Discovery Conference: Abstract Book, Latvia, Rīga, 27-29 August, 2015. Rīga: 2015, pp.123-123.
ID 20626