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The Synthesis Of Thiourea Derivatives In PEG And Aminoalkyl-2-Naphthol In Presence Of Sulfonylacid Catalyst Supported By Polymer

Posted on:2010-05-28Degree:DoctorType:Dissertation
Country:ChinaCandidate:Z ZhangFull Text:PDF
GTID:1101360278997215Subject:Polymer Chemistry and Physics
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The ecological and durative environment has become the focus of the world with the progress of society. Environmental economics has become an important steering wheel for technological innovation. So, development of environmentally friendly chemical synthesis has been obtained considerable interesting both in academic and industrial research. The replacement of toxic and volatile organic solvents as reaction media or an efficient catalyst with environmentally acceptable alternatives are an area of tremendous importance in modern organic synthesis. Basing the review about solid-phase synthesis with simple separation, the liquid phase organic synthesis supported by the solution polyethylene glycol and the chemical reactions in the medium of PEG, herein we are going to study the synthesis of 1-amidoalkyl-2 -naphthols in presence of the solution catalyst or the solid catalyst and the synthesis of thiourea in PEG-400 medium. Three branches are included in this paper.1. In PEG-400 treatment of the corresponding acylchloride with ammonium thiocyanate, aromatic amines or arylhydrazide gave 12 N-aryl-N/-(5-(2/-nitrophenyl) -2-furoyl)-thioureas, 11 1-aryloxyacetyl-4 -(5/-(2// -nitrophenyl)-2/-furoyl) -thiosemicarbazides, 14 N-aryl-N' -(2-benzofuroyl)-thioureas, 9 1-aroyl-4 -(2'-benzofuroyl) -thiosemicarbazides, and 12 N-aryl-N/-benzoylthioureas. A total of 58 compounds have been synthesized. And all these compounds were characterized by Elemental analysis, IR and 1H NHR. The merits of the method is non-toxic PEG-400 as the solvent, at the same time doubles as a phase transfer catalyst. The mission is finished with short time, mild conditions, high yields and simple work-up.2. Polymer bound sulfonic acid was prepared on nonsoluble polystyrene–poly(ethylene glycol) (PS–PEG) resin. The PS–PEG-bound sulfonic acid exhibited good catalytic activity in the synthesis of 1-amidoalkyl-2-naphthols via a three-component condensation of 2-naphthol, ureas/amides, and aldehydes, with good yield and good recyclability. This method presents are markable technique toward an efficient synthesis of 1-amidoalkyl-2-naphthols.Another efficient and environmentally friendly process for the synthesis of 1-amidoalkyl-2-naphthols via the same three-component condensation reaction using soluble poly(ethyleneglycol)-bound sulfonic acid has been developed. The functionalized poly(ethylene glycol) acted simultaneously as catalyst in the condensation. The workup was easy, and the products were obtained in good to excellent yields and high purities.3. Diselenides were synthesized by the reaction of sodium borohydride, selenium powder and halohydrocarbon in the media of PEG-400. At the same time, the PEG-400 do the role of surfactant. Sodium borohydride and halohydrocarbon can be dissolved while it ensure good energy change and mass transfer with the reaction. The toxic hydrogen selenide gas was reduced, while the utilization of sodium borohydride was over a lot when the PEG-400 instead of ethanol. More importantly, ethanol could cause decomposition of sodium borohydride, and PEG-400 combines the dual nature of alcohol and ether, The former guarantees the expected reaction to be able to successfully carry out when alkali was present. The latter weakens the decomposition of sodium borohydride.
Keywords/Search Tags:Green synthesis, Polyethylene glycol, Thiourea, Thiosemicarbazide, Supported sulfonic acid catalyst, 1-Amidoalkyl-2-naphthol, Three components, Diaryl diselenides
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