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Constructions Of Quinazoline Derivatives And Benzo[a]fluorenols Via C-H Bond Activation And Tandem Reactcions

Posted on:2015-02-13Degree:MasterType:Thesis
Country:ChinaCandidate:M J ZengFull Text:PDF
GTID:2181330431998551Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Benzofluoren and quinazoline can be found in many natural occurring products,which are commercially important in biology, pharmaceuticals and many other fields.Therefore, many organic chemists focus their interest on the synthesis of this class ofcompounds.As one of the most efficiency strategy in diversity-oriented synthesis,tandemreaction provides several advantages such as environmental friendliness and highefficiency. At the same time, tandem reactions that encourage the simple material andrelatively less synthetic step to create novel products with an optimal number ofmolecular diversity and complexity.C-H bond is one of the most common functional-group among organic compound.Transition metal-catalyzed C-H bond functionalization is one of the most efficient,convenient and economic methodologies for the systhsis of target compounds basedon easily available starting materials with short synthetic routes, Therefore, manyorganic chemists focus their interest on the formation of C-C bond by transition metal-catalyzed C-H bond functionalization.The thesis is mainly focused on the synthesis of benzofluoren derivatives viatandem reactions and quinazoline derivatives via C-H bond functionalization.Firstly, A facile and novel silver tetrafluoroborate catalyzed electrophilic cascadecyclization reaction to generate halo-substituted benzo[a]fluorenols under mildconditions is disclosed. Good chemical selectivity and mild reaction conditions wereinvolved in the transformation. The halidecontaining benzo[a]fluorenols could befurther elaborated via palladium-catalyzed cross-coupling reactions to gain complexcompounds.Quinazoline was used as a directing group for palladium-catalyzed ortho-mono-arylation quinazoline via C-H bond activation. The reaction proceeded well with abroad substrate scope in a highly regioselective manner to provide a direct way toaccess highly functional quinazoline core structure derivatives.
Keywords/Search Tags:tandem reaction, benzofluorenols, electrophilic cyclization, C-Hbond functionalization, arylation, quinazoline
PDF Full Text Request
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