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Constructions of Several Natural Product-like Compounds Via Tandem Reactions

Author: QiuGuanYinSheng
Tutor: PengYiYuan
School: Jiangxi Normal University
Course: Organic Chemistry
Keywords: Tandem Reaction 1 - methylene indenyl ring skeleton Indole skeleton Quinazoline derivatives
CLC: O621.2
Type: Master's thesis
Year: 2011
Downloads: 26
Quote: 0
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Abstract


1 - methylene- indene ring , an indole ring , a quinazoline ring skeleton is the unit of the core structure of many natural products , widely present in the drug molecule and the therapeutic agent . Therefore , many chemists are working to develop construction methods based on such core skeleton , our group tried from several simple raw materials , synthesis of the above three types of skeleton . This paper describes a tandem reaction to construct 1 - methylene indene Central , indole ring, quinazoline ring skeleton method . First, we develop Cs 2 CO 3 Promoted o - alkynyl benzaldehyde , malononitrile , three-component indole addition reaction through the series build 1 - methylene base indene ring skeleton . In addition, we also studied as raw materials in a simple Knoevenagel condensation product with imidazole or benzimidazole , t -BuOK can promote the substituted group of different indene ring method , this method can also be efficient synthesis of 1 - methylene indene ring derivative thereof. Secondly, we have reported a series Beckmann rearrangement and intramolecular cyclization reaction to efficiently build indole compounds . Acetophenone oxime starting from o - alkynyl phenyl trichloro- cyanuric (CNC) , the small organic molecules to catalyze the Beckmann rearrangement to give the amide intermediate , and then added directly to the transition metal salt (PdCl 2 ( MeCN) 2 < / sub >) as a Lewis acid to activate the acetylene bond intramolecular cyclization substituted indole compounds ; if added ( PdCl 2 (MeCN) 2 ) as a Lewis acid, of CuCl 2 as an oxidizing agent can be synthesized by a 3 - chloro - indole compound . Finally , the fourth chapter study starting from easy to get raw materials quinazolin-4 - one , using methyl benzene sulfonyl chloride (TsCl) as the activator of the C-OH , under the premise of without isolation of intermediates , series SN2 substitution reactions , with the the thiophenol reaction to obtain 4 - thioether quinazoline skeleton ; series metal Suzuki coupling reaction , with an aryl boronic acid to give 4 - aryl - substituted quinazoline skeleton compounds .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds
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