Coumarin and triazole derivatives have been extracted from plants, seeds and roots for ages in traditional methods. As the science advances, unknown profits of biologically active compounds have been investigating by researchers in modern laboratories. Extracts of natural sources containing coumarin and triazole derivatives were found to be potential natural medicines. The organic structures of these molecules bear extraordinary biological activities such as inflammatory activity, anti-HIV activity, treatment of cold and rheumatism and anticancer activity. In this study, attemps toward the synthesis of coumarin-triazole hybrids will be presented. At first attempt, starting from 2-amino-5-chlorophenol, coumarin-triazole hybrids were tried to be obtained through ynone intermediates, yet the experiments on acquiring corresponding ynone intermediates were failed. As second approach, 4-iodocoumarin and 4-bromocoumarin derivatives were tried to be synthesized from 4-hydroxycoumarin derivative that was acquired from acetyl salicylic acid, and the attempts were failed again. As an alternative, 4-tosylcoumarin derivative was used as pseudo halogenated coumarin derivative with triazole derivatives that were prepared starting from 4-chlorobenzyl azide. However, the failure was witnessed after all trials. In further trials, obtaining an internal alkyne as Sonogashira product from 4-tosylcoumarin derivative was the first step of another approach to produce desired hybrid structures. Unfortunately, in the second step a click chemistry between Sonogashira product and 4-cholorobenzyl azide was failed to form corresponding hybrid structures. Finally, possible Heck reaction was studied between coumarin derivative and 5-iodo-1,2-disubstituted-1,2,3-triazole derivative, that was also failed to obtain desired coumarin-triazole hybrid.