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Enaminones-based Multicomponent Reactions For The Synthesis Of Pyrroles

Posted on:2014-08-28Degree:MasterType:Thesis
Country:ChinaCandidate:Q Y LiFull Text:PDF
GTID:2181330422974536Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The discourse includes four parts.The first part involves the development of enaminones-based multicomponent for thesynthesis of heterocyclic compounds home and abroad, including multicomponet one-pottandem strategy and direct functionalization of sp3C-H bond. In addition, this part alsointroduces the synthesis of substituted Pyrroles, the significance and base of the selection ofthe subject, the original points and the research techniques.The second part involves the challenging annulation of enamines with arylglyoxalmonohydrates and acetic acid as the solvent yielding multifunctionalized tricyclic fusedpyrroles, and the complete anti-diastereoselectivity is achieved in the reaction. The novelty ofthe present domino reaction is shown by the fact that the pyrrole skeleton is formed and itsfunctionalization is simultaneously achieved via metal-free allylic sp3-C-H bonds activation inan intramolecular manner in a one-pot operation.The third part involves a multicomponent synthesis of fully substituted pyrroles. Thereaction is easy to perform simply by mixing three common reactants (enamines, arylglyoxalmonohydrates, indoles or thioles) in acetic acid under microwave heating. The reactionproceeds at fast rate and can be finished within20min, which makes workup convenient andexcellent chemical yields. The resulting fully substituted pyrroles are important structuralattribute in many bioactive natural products, therapeutic compounds, and new organicmaterials.The forth part describes an efficient three-component domino strategy for the synthesisof multifunctionalized tetracyclic indeno[1,2-b]indole derivatives with different substitutedpatterns successfully. The first pathway involves novel sequential methyl migration,aromatization, and esterification, while the second reaction leads to compounds with high syndiastereoselectivity. Both reactions show attractive features including mild conditions,convenient one-pot operation, short periods of15-32min, and excellent regio-and/orstereoselectivity.The structures of the products are determined by IR,1H NMR, Furthermore, thestructures of some products are confirmed by X-ray analysis. The microwave-assistedreactions mentioned above have advantages of shorter reaction time, higher yields and easierwork-up as well as environmentally friendly. Therefore, new and environmentally friendlymethods for the synthesis of these important compounds are provided.
Keywords/Search Tags:Enaminones, Multi-component Reactions (MCRs), Pyrrole Derivatives
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