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.