Deniz Hakan, Yıldız Tülay, Başpınar Küçük Hatice
Department of Chemistry, Organic Chemistry Division, Istanbul University-Cerrahpaşa, Avcilar, Istanbul 34320, Turkey.
ACS Omega. 2024 Mar 8;9(11):12596-12601. doi: 10.1021/acsomega.3c07150. eCollection 2024 Mar 19.
In this study, a series of halogen-substituted thioxanthenes were synthesized because the most important and biologically active derivatives of xanthenes are thioxanthenes. In order to obtain new thioxanthene derivatives, first, the starting molecules were synthesized by the appropriate reaction methods in two steps. The intramolecular Friedel-Crafts alkylation (FCA) method was used to convert the prepared three aromatic substituted starting alcohol compounds to their corresponding thioxanthenes by cyclization. For the intramolecular FCA reaction of secondary alcohols, which are the starting compounds (-), organic Bro̷nsted acids, which require more innovative, easier, and suitable reaction conditions, were used instead of halide reagents with corrosive effects as classical FCA catalysts. Trifluoroacetic acid was determined to be the organocatalyst with the best yield. Therefore, some original 9-aryl/alkyl thioxanthene derivatives (-) were synthesized using the optimized FCA method. In addition, a new sulfone derivative of thioxanthene was prepared by performing the oxidation reaction with one of the obtained new thioxanthene . Thioxanthenes and their derivatives are important heterocyclic structures that contain pharmacologically valuable sulfur and are used in the treatment of psychotic diseases such as Alzheimer's or schizophrenia, as well as a number of potent biological activities.
在本研究中，合成了一系列卤代噻吨，因为呫吨最重要且具有生物活性的衍生物是噻吨。为了获得新的噻吨衍生物，首先通过适当的反应方法分两步合成起始分子。采用分子内傅克烷基化（FCA）方法，通过环化将制备的三种芳基取代的起始醇化合物转化为相应的噻吨。对于作为起始化合物（-）的仲醇的分子内FCA反应，使用需要更具创新性、更简便且合适反应条件的有机布朗斯特酸，而不是具有腐蚀性的卤化物试剂作为经典的FCA催化剂。三氟乙酸被确定为产率最高的有机催化剂。因此，使用优化的FCA方法合成了一些原始的9-芳基/烷基噻吨衍生物（-）。此外，通过对所获得的一种新噻吨进行氧化反应，制备了一种新的噻吨砜衍生物。噻吨及其衍生物是重要的杂环结构，含有具有药理学价值的硫，可用于治疗阿尔茨海默病或精神分裂症等精神疾病，以及许多强大的生物活性。
