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The One-pot, Four-component Synthesis Of5H-Spiro [Benzo [7,8] Chromeno [2,3-c] Pyrazole-7,3’-indoli Ne]-2’,5,6(9H)-trione Derivatives Catalyzed By MgCl2and The Synthesis Of2,2-bis(1H-Indol-3-Yl)-2H-acena-Phthen-1-One Catalyzed By Ca

Posted on:2015-08-31Degree:MasterType:Thesis
Country:ChinaCandidate:H B DangFull Text:PDF
GTID:2181330467951254Subject:Organic Chemistry
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The indole framework is common in a wide variety of pharmacologically and biologically active compounds. Furthermore, sharing of the indole3-carbon atom during the formation of spiroindoline derivatives enhances the biological activity significantly. The spiro-oxindole system is the core structure of some pharmacological agents and natural alkaloids.The naphthoquinone moiety is found in many natural products, most of them exhibit interesting biological activities. Also, the naphthoquinone moiety is involved in a wide variety of biochemical processes, including electron transport and oxidative phosphorylation. Thus, quinones and their derivatives have become attractive targets in organic synthesis.Bisindolylalkanes (BIAs) display diverse biological and pharmacological activities. The development of high-throughput methods for the synthesis of bisindolylalkanes (BIAs) remains a topic of paramount importance in the field of organic synthesis.In this article, the first chapter is litetature review, the second chapter introduces detailedly the one-pot, four-component synthesis of1H-spiro[benzo[6,7]chromeno [2,3-c]pyrazole-4,3’-indoline]-2’,5,10-trione derivatives catalyzed by MgCl2, the third chapter introduces the synthesis of5H-spiro[benzo[7,8]chromeno[2,3-c]pyrazole-7,3’-indoline]-2’,5,6(9H)-trione derivatives catalyzed by camphorsulfonic acid (CSA).The main work contains:(1) We studied the synthesis of5H-spiro[benzo[7,8]chromeno[2,3-c]pyrazole-7,3’-indoline]-2’,5,6(9H)-trione derivatives by a one-pot, four-component reaction of hydrazine hydrate, β-keto ester, isatins and2-hydroxyna-phthalene-1,4-dione. The effects of catalyst, catalyst-loading, solvent and tempetature on the model reaction were evaluated. The proper reaction condition was found out. Under the optimized condition,22new compounds were synthesized, the structures of all products were established by IR spectra,1H NMR spectral data,13C NMR spectral data, MS (HRMS or ESI-MS) analysis and elemental analysis.(2) We studied the synthesis of2,2-bis(1H-indol-3-yl)-2H-acenaphthen-l-one derivatives via a reaction of acenaphthenequinone and indoles. The effects of catalyst, catalyst-loading, solvent and tempetature on the model reaction were evaluated. The proper reaction condition was obtained. Under the optimized condition,8compounds were synthesized, in which6compounds were known products, and2compounds were new. The structures of all products were established by IR spectra,1H NMR spectral data,13C NMR spectral data, EI-MS analysis and elemental analysis.
Keywords/Search Tags:multicomponent reaction, 1,2-naphthoquinone, spiro-oxindolecompounds, camphorsulfonic acid (CSA), bisindolylalkanes (BIAs)
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