Synthesis of ferrocenyl substituted pyrazoles by Sonogashira and Suzuki-Miyaura cross-coupling reactions

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Tezin Türü: Yüksek Lisans

Tezin Yürütüldüğü Kurum: Orta Doğu Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Türkiye

Tezin Onay Tarihi: 2010

Öğrenci: SEDEF KARABIYIKOĞLU

Danışman: METİN ZORA

Özet:

Pyrazoles constitute one of the most important classes of heterocyclic compounds due to their interesting chemical and biochemical features. Researchers have studied many pyrazole containing structures for almost over a century in order to investigate the various biological activities possessed by these molecules. A new and important trend in these studies is to produce ferrocenyl substituted pyrazoles since ferrocene attracts considerable interest in the research field of organometallic and bioorganometallic chemistry because of its valuable chemical characteristics like high stability, low toxicity and enhanced redox properties. Moreover, the results of the studies focusing on ferrocenyl compounds have been quite promising. Therefore, the scope of this project involves the combination of the essential structural features of pyrazoles with a ferrocene moiety, which could provide new derivatives with enhanced biological activities. In the course of the project the synthesis of new pyrazole derivatives was performed through Sonogashira and Suzuki-Miyaura cross-coupling reactions of 5-ferrocenyl-4-iodo-1-phenyl-1H-pyrazole with terminal alkynes and boronic acids respectively in the presence of a catalytic amount of PdCl2(PPh3)2. Although Sonogashira and Suzuki-Miyaura coupling reactions are well known in literature, they were not studied in much detail with multi-substituted pyrazoles. This also revealed the requirement of the reinvestigation of the reactions and improvement of the yields of pyrazoles by optimizing the reaction conditions.