Synthesis of new derivatives of symmetric bisarylidene of cyclic ketones based on triazole ring

Aldol condensation is an important reaction for the C-C bond formation in most of carbonyl compounds. Among this kind of reactions, Claisen-Schmidt condensation of aryl halides with cycloalkanones is a major procedure for the synthesis of α,α - bis(arylmethylidene) cycloalkanones [1]. Bisarylidenes of cyclic ketones have diverse synthetic applications in preparation of different compounds such as precursors of pharmaceuticals, pesticides, anti-fungal, anti-bacterial and anti-inflammatory agents, as well as polymeric units (synthons) of liquid crystals [2]. On the other hand, click chemistry is an efficient and selective method for the synthesis of triazoles through a 1,3-dipolar cycloaddition of azide and alkyne. Triazol derivatives have several biological and pharmaceutical properties, such as anti-cancer and anti-HIV effects[3]. Due to the importance of bisarylidenes and triazoles, in this project has been attempted to synthesize new derivatives of symmetric bisarylidenes of cyclic ketones based on triazol ring. For this purpose, at first triazol-based aldehydes (1) were prepared via click reaction between propargyloxybenzaldehydes and benzyl azides. Then, aldol condensation of these compounds with different cylic ketones (2) led to the synthesis of corresponding triazol-based bisarylidenes (3).