Synthesis of 3,5-diamino isoxazole substituted triarylmethane compounds

Isoxazoles are five-membered heterocyclic aromatic compounds. The given examples in the literature show that their synthesis and reactions have a wide importance. The reason for this is that the isoxazole compounds find applications in wide areas such as biological activity, medicine and agriculture. Such structures having broad applications are gaining importance in organic synthesis chemistry. After the first synthesis of isoxazole through the reaction of hydroxylamine and benzoyl acetone by Ceresole in 1884, many synthesis methods have been developed until today. These structures can be synthesized by different methods and then easily functionalized. According to the aryl and heteroaryl components on triarylmethanes, they have found wide use in cell imaging as a fluorescence sensor, as building blocks in natural products, medicine, material chemistry and ligands. Although various synthesis methods are used to obtain triaryl methanes, the most preferred method is the Friedel-Crafts reaction. Considering the importance of each triarylmethane and isoxazole structure in applications, in the course of this thesis it was planned to synthesize triarylmethanes with aryl and heteroaryl groups that have the structural features of both systems. Benzylidenemalononitrile derivatives were chosen as they are the most suitable starting structures to reach triaryl groups to be attached on the same carbon atom. In the first step, these compounds were synthesized by the Knoevenagel condensation reaction of aryl aldehydes and malononitrile. These structures, which are good Michael acceptors, were attached to the second aryl group by the addition of pyrrole or indole. In the last step, the functionality of malononitrile on the molecule was used for the formation of isoxazoles. The products synthesized by Michael addition reactions reacted with hydroxyl amine and new triarylmethane compounds with isoxazole, 2-pyrrolyl or 3-indolyl structures were obtained.