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Through A Number Of Series Synthesized By The Reaction With Isoquinoline Skeleton Compounds

Posted on:2012-12-17Degree:MasterType:Thesis
Country:ChinaCandidate:H RenFull Text:PDF
GTID:2191330335998406Subject:Chemical Engineering
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This dissertation mainly centers on methodology development for the construction of isoquinoline compounds via tandem reactions. It is divided into two parts:(1) three-component reaction of N'-(2-alkynylbenzylidene)hydrazide, a, (3-unsaturated carbonyl compound, with bromine; (2) silver triflate-catalyzed tandem reaction of 2-alkynylbenzaldoxime with aryne.Different outcomes were generated under different conditions for the three-component reaction of N'-(2-alkynylbenzylidene)hydrazide,α,β-unsaturated carbonyl compound, with bromine.6-BromoH-pyrazolo[5,1-α]isoquinoline was obtained when the reaction was performed in NMP at 70℃in the presence of DABCO as base, while 6-bromo-1,2,3,10b-tetrahydropyrazolo[5,1-α]isoquinoline was afforded when the reaction occurred in DMAc at 10℃in the presence of K3PO4 as base.In the meantime, a novel and unexpected reaction of 2-alkynylbenzaldoxime with aryne in the presence of silver triflate (10 mol%) under mild conditions was discovered. This reaction proceeded through 6-endo-cyclization, [3+2] cycloaddition and rearrangement, leading to 2-oxa-6-aza-bicyclo[3.2.2]nona-6,8-diene derivatives in moderate to good yields.
Keywords/Search Tags:natural product-like compound, isoquinoline, N'-(2-alkynylbenzylidene) hydrazide, 2-alkynylbenzaldoxime, α,β-unsaturated carbonyl compound, aryne, tandem reaction
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