Potential Biologically Active Agents, XXVII: Synthesis of Some 4‐Substituted Phenylmercaptoacetic Acids

Abstract

Condensation of 4-(3H)-quinazolinone (2) with 4-(aminopheny1)-mercaptoacetic acid under the conditions of the Mannich reaction furnished compounds 3a and 3b. Reaction of 4 with 4-(amino-phenyl)mercaptoacetic acid yielded 5 which when treated with aryl aldehydes gave 6. Similarly, compounds 8 were obtained from 7.Potentiell biologiscb aktive Verbindungen, 27. Mitt.l) Die Synthese einiger 4-substituierter PheuylmercnptoessigsiiurenDie Kondensationen von 4-(3H)-Chinazolinon (2) rnit 4-Amino-phenylmercaptoessigsaure unter den Bedingungen der Mannich Reaktion lieferte 313 und 3b. Die Reaktion von 4 mit 4-Aminophenylmercaptoessigsaure ergab 5, das mit Arylaldehyden 6 ergab; ahnlich wurde 8 aus 7 dargestellt.Quinazolones are reported to possess good central nervous system depressant properties2). Some 2,3-disubstituted quinazolones were in~estigated~)~) and it was found that 2-methyl-3-o-tolyl-4-quinazolone is a potent anticonvulsant drug 5 ) . y-Aminobutyric acid (GABA) is considered as a central inhibitory neuroharmonal modulatofi) and some carboxylic acids have been reported to possess significant anticonvulsant properties'). It was speculated that the presence of a carboxylic group in the substituted quinazolones might result in better anticonvulsant activity. These observations led us to synthesis few substituted 2-rnethyl-(phenyl and styryl)-3-[4(3H)-quinazolyl]-phenyl-4-mercapto-acetic acids and related compounds for pharmacological screening. + Senior Alexander von Humboldt Stiftung Research Associate,

Energy‐Efficient Synthesis of Haloquinazolines and Their Suzuki Cross‐Coupling Reactions in Propylene Carbonate

“…Three approaches were used to synthesise haloquinazolines by Suzuki‐Miyaura cross‐coupling reaction demonstrated in Scheme 1. First, the reaction of 5‐bromoanthranilic acid ( 1 ) in acetic anhydride was used to form compound 2 [42] with a benzoxazine ring. Next, the latter was reacted with aqueous ammonia resulting in 6‐bromo‐2‐methylquinazolinone 3 [43] .…”