Synthesis, antibacterial activity, and fluorescence properties of a novel series from [2,4-dioxochromen-3(4H)methyl]amino acid

• Published in: Research on chemical intermediates 2018-03, Vol.44 (3), p.1551-1567
• Main Authors: Faty, Rasha A. M., Mourad, Asmaa K., Abd Elmotaleb, Ramadan M., Radewan, Rasha M.
• Format: Article
• Language: English
• Subjects: Absorption; Acetic acid; Amines; Amino acids; Bacteria; Catalysis; Chemistry; Chemistry and Materials Science; Emission analysis; Fluorescence; Inorganic Chemistry; Maleic anhydride; Nucleophiles; Physical Chemistry; Synthesis
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-017-3184-0

A new solvent-free method for synthesis of starting compounds 2,4-dioxochromen-3(4 H )methyl amino acetic acid derivatives 1a – e via a green approach is reported. Also, the behavior of compound 1a towards various nitrogen nucleophiles such as primary amines, hydrazine hydrate, and hydroxylamine hydrochloride to give corresponding compounds 2 – 4 was studied. Furthermore, chlorination of compound 1a using a mixture of PCl 5 /POCl 3 to yield acid chloride derivative 5 and the reaction of the latter compound 5 with various amino acids to obtain dipeptide compounds 6a – e are described. Moreover, cyclization of compound 1a in alkaline medium to afford dihydrochromeno[3,4- c ]pyrrole-1-carboxylic acid 7 and cyclization of 6b in acidic medium, namely Ac 2 O, to yield piperazine derivative 8 are reported. Also, reaction of compound 1a with maleic anhydride in dioxane to afford Diels–Alder adduct 9 , which posteriorly reacted with hydrazine hydrate to give 10 , was investigated. Most of the newly synthesized compounds were screened against Gram-positive and Gram-negative bacteria, with compound 5 exhibiting the maximum inhibition zone towards all four types of bacteria. In addition, the absorption and fluorescence emission of some of the substituted coumarins were studied in dioxane, revealing that the substituents altered both the absorption and fluorescence emission maxima.