Mannich reaction with multi component one-pot method in different medium
2012
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Advisor: Prof. Dr. Zuhal Turgut
Abstract (EN)
Mannich reactions which are used in synthesis of biologically important heterocyclic compounds and various ß-aminoketones and ester and also in preparing multi-functional synthetic building blocks having nitrogen have been continuously showing development. Recently, the usage of triflates in aqueous or solvent-free medium instead of Lewis acid catalyst in Mannich reactions is attracting interest.In recent studies, water is not only environmentally sensitive, inexpensive and abundant material but it also satisfies unique selectivity and easiness of reaction. In comparison to alternatives, bismuth(III) triflates are attractive catalysts with their cost effective property and low toxicity. The aqueous micelle medium of non-ionic surface active agent (surfactant) Triton X 100 gives highly good results due to its capability of increasing solubility of initial materials.In literature, it was well shown that in almost all organic reaction systems, comparing to reactions done in classical methods, the reactions held by ultrasonic or microwave systems are completing with mild reaction conditions and high yields in shorter reaction times.In this study, for three component direct type Mannich reaction, four different methods were tested: classical, ultrasound assisted, classical in aqueous micelle medium of surfactants and microwave assisted. Anti-selective property new ß-aminoketone compounds of heterocyclic or substituted aromatic aldehyde, substituted aromatic amine and cyclohexanone were synthesized with the catalyst of Bi(OTf)3.4H2O in a aqueous medium and short reaction time with high yield. The structures of synthesized compounds were clarified with analysis results of FTIR, 1HNMR, 13CNMR, mass spectroscopy and elemental analysis. In addition, the mutagenic, antimutagenic and antitumor activity studies were performed in the scope of biological investigations.
Author
Dr. S. Arda Öztürkcan
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How to Cite
S. Arda Öztürkcan (Doctorate thesis). Mannich reaction with multi component one-pot method in different medium, 2012, Yıldız Technical University.
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