Domino Knovenagel Condensation/Nazarove Reaction Of 1,3-Diphenylactetone

There has been increasing interest in highly efficient and environmentally acceptable synthetic methods in modern organic chemistry. In this context domino reactions have proven to be very effective and attractive, because they can form multiple bonds and stereocenters in a single reaction without the need to isolate intermediates. Knoevenagel condensation and Nazarov cyclization are fundamental organic reactions in the chemical synthesis. They have been used as the key steps in the total synthesis of natural products and biologically active compounds.The main work of the thesis is the investigation of domino reaction of 1,3-diphenylacetone with aldehydes, which provided a novel synthetic methodology for the construction of polysubstitutent cyclopentenone and cyclohexenone derivatives. Catalyzed by piperidine and acetic acid, cyclopentenones were obtained by domino Knoevenagel condensation/Nazarov cyclization reactions of 1,3-diphenylacetone and aryl aldehydes; cyclohexenones were resulted from domino Michael addition/Knoevenagel condensation reaction of 1,3-diphenylacetone and cinnamaldehyde.The synthesized compounds were characterized by ¹H NMR, ¹³C NMR and high-resolution mass spectra (HRMS). The mechanism of the reaction was also discussed, which is useful for further research.