Cyclooctanone reacts with arylidene malononitrile to afford cycloocta[b]pyridine-3-carbonitrile derivatives 2a-b. 2-Amino-4-(4-chlorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile 2a reacts with benzoyl chloride and acetic anhydride to afford compounds 3 and 4 respectively. N-(4-(4-Chlorophenyl)-3-cyano-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl)benzamide 3 and N-(4-(4-Chlorophenyl)-3-cyano-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl)acetamide 4 reacts with hydrazine hydrate to afford compounds 5a,b. 5-(4-Chlorophenyl)-4-imino-2-phenyl-6,7,8,9,10,11-hexahydrocycloocta[5,6]pyrido[2,3-d]pyrimidin-3(4H)-amine 5a and 5-(4-Chlorophenyl)-4-imino-2-methyl-6,7,8,9,10,11-hexahydrocycloocta[5,6]pyrido[2,3-d]pyrimidin-3(4H)-amine 5b reacts with D-glucose and D-ribose to produce compounds 6a-d. Compounds 6a,b react with acetic anhydride to afford acetylated derivative 7a,b. Anticancer profile of the prepared compounds were tested against three cell lines namely A-549, CaCo-2, and HT-29.