Design, synthesis, characterization, and antimicrobial evaluation of the novel 2-heteroarylchromeno[2,3-d]pyrimidines

Abstract

The present work is directed to synthesize and evaluate the antimicrobial activity of some novel 2-heteroarylchromeno[2,3-d]pyrimidines. 2-(6,8-Dimethylchromon-3-yl)-8-methoxy-4H-chromeno[2,3-d]pyrimidine-4,5(3H)-dione (4) was successfully synthesized and utilized as a building block to produce a variety of heterocyclic compounds. 2-(4-Pyrazolyl/isoxazolyl)chromeno[2,3-d]pyrimidines 5–7 were obtained from the reaction of compound 4 with hydrazine hydrate, phenylhydrazine, and hydroxylamine, respectively. Also, 2-(6-pyrimidinyl)chromeno[2,3-d]pyrimidines 8–12 were efficiently prepared from reacting compound 4 with guanidine, cyanoguanidine, thiourea, acetamidine, and benzamidine, respectively. Further, chromeno[2,3-d]pyrimidines linked diazepine 13, benzodiazepine 14, benzoxazepine 15 and benzothiazepine 16 were also synthesized. The synthesized compounds were examined for their antimicrobial efficiency. Pyrazolylchromeno[2,3-d]pyrimidines 5 and 6 showed the best activity against all kinds of microorganisms. Structures of the synthesized compounds were validated using analytical and spectral data.

GRAPHICAL ABSTRACT

Keywords:

• Chromeno[2,3-d]pyrimidines
• chromone
• nitrogen heterocycles
• nucleophilic reactions
• RORC

Additional information

Funding

The authors extend their appreciation to Princess Nourah bint Abdulrahman University Researchers Supporting Project number (PNURSP2023R103), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia.