Synthesis and Biological Evaluation of Novel Quinazoline, Chromene and Chromeno[2,3-d]pyrimidine Derivatives

Yousif, Mahmoud Nabil Mahmoud; El-Gazzar, Abdel-Rhman B. A.; Hafez, Hend N.; Yousif, Nabil M.

doi:10.21608/ejchem.2022.113647.5161

Synthesis and Biological Evaluation of Novel Quinazoline, Chromene and Chromeno[2,3-d]pyrimidine Derivatives

Document Type : Original Article

Authors

Photochemistry Department, National Research Centre, Cairo, Egypt.

10.21608/ejchem.2022.113647.5161

Abstract

2-(2-Chlorobenzylidene)cyclohexan-1-one reacts with various organic reagents. It reacts with guanidine and aminoguanidine to give the quinazoline derivatives 1a,b. 2-(2-Chlorobenzylidene)cyclohexan-1-one reacts with urea and malononitrile to afford chromene derivatives 2 and 3 respectively. Chromene derivative 3 reacts with formic acid and acetic acid to give chromeno[2,3-d]pyrimidine derivatives 4a and b respectively. Also, chromene derivative 3 reacts with acetic acid in presence of sulphuric acid to afford the chromene derivative 5. Chromene derivative 5 reacts with benzoyl chloride to afford corresponding benzoyl derivative 6. Chromene derivative 3 reacts with triethyl orthoformate to afford chromene derivative 7 which reacts with hydrazine hydrate to afford chromeno[2,3-d]pyrimidine derivative 8. The Quinazoline derivative 1b reacts with ribose and glucose to produce quinazoline derivatives 9a,b which were acetylated using acetic anhydride to give quinazoline derivatives 10a and b respectively. Some of the prepared compounds are screened for anticancer activity against doxorubicin as reference drug.

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