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Studies on the Synthesis of Benzotriazoles and 4-Qquinolones

Author: LiuQiLun
Tutor: ZhuYongMing
School: Suzhou University
Course: Medicinal Chemistry
Keywords: Benzotriazole copper catalyzed Quinolone metal-free one-pot
CLC: R914
Type: Master's thesis
Year: 2011
Downloads: 15
Quote: 0
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Abstract


Only one out of the top 10 bestseller prescription drugs is non-heterocyclic. With more and more people perceiving the idea of sustainable development, it’s imperative to develop greener synthetic methodologies, i.e. more economic and efficiency. The thesis consists of two parts, mainly on the establishment of nitrogen heterocycles via intramolecular amination reactions.The first part centers on the synthesis of benzotriaozles which were obtained in high yield via the intramolecular amination cyclization of corresponding triazenes using CuI as the catalyst, 1,10-phenanthroline the ligand, and sodium tert-butoxide the base, in DMSO at 130℃for 10 h. The methodology addresses the issue of isomers caused by tautomerism, and is tolerant of EWGs, EDGs and steric hindered groups.The second part describes a metal-free one pot strategy for the synthesis of 4-quinolones, via intramolecular amination cyclization of schiff base that is generated in situ from aldehydes and amines in DMSO. The strategy is characterized by high yield and wide functionality tolerance, e.g. electron-withdrawing, electron-donating and steric hindered groups, requires no isolation of intermediates and is therefore applicable to library synthesis.

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