Work

Synthesis of several 2,7-dibromoacridine derivatives, including 4-[2-(succinimidyloxycarbonyl)ethyl]phenyl 2,7-dibromo-10-methylacridinium-9-carboxylate trifluoromethanesulfonate

Year: 2024

Type: article

Abstract: The reaction of bis(4-bromophenyl)amine and oxalyl chloride gave N-(4-bromophenyl)-5-bromoisatin, which on treatment with potassium hydroxide yielded 2,7-dibromoacridine-9-carboxylic acid.Treatment of acridine-9-carboxylic acid with freshly redistilled thionyl chloride followed by reaction with benzyl 3-(4hydroxyphenyl)propanoate gave the corresponding benzyl ester.Hydrolysis of the benzyl ester gave the corresponding acid, which, on reaction with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide, gave the corresponding ester.Finally, methylation of the N-hydroxysuccinimide ester gave the corresponding 10-methylacridinium trifluoromethanesulfonate.

Source: ARKIVOC

DOI: 10.24820/ark.5550190.p012.307

Authors: Keith Smith, Gamal A. El-Hiti

Institutions: Cardiff University, King Saud University

Language: English

Topic: Synthesis and Reactivity of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Cardiff University, King Saud University

Award: G7579582587