Synthesis of Five Membered Nitrogen Containing Heterocycles Including Pyrrole, Imidazole and Tetrazole in Aqueous Media

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Khalili, Behzad | 2010

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Type of Document: Ph.D. Dissertation
Language: Farsi
Document No: 40853 (03)
University: Sharif University of Technology
Department: Chemistry
Advisor(s): Mahmoudi Hashemi , Mohammad
Abstract:
This thesis contains four chapters. In first chapter the role of water in organic reactions as a ecofriendly solvent, computational chemistry and dynamic nuclear magnetic resonance were studied. In the second chapter synthesis of new 4-hydroxy pyrrole derivatives in water were reported. For the synthesis of these compounds arylglyoxal derivatives, 1,3-dicarbonyl compounds and ammonium acetate were used. The reaction conditions are very mild. The third chapter contains the synthesis of new (4 or 5)-Aryl-2-aryloeil-(1H)-imidazole compounds in aqueous media. We also investigated the tauto-isomerisation of isomeric imidazoles during this reaction using DNMR technique. In forth chapter a practical procedure for the regioselective synthesis of 5-amino-1-aryl-(1H)-tetrazoles in aqueous media was introduced. This synthesis carried out with the use of arylcyanamides and sodium azids and zirconium oxy chloride as Lewis acid catalyst
Keywords:
Computational Chemistry ; 5-Aryl-1H-Pyrrole ; Tautoisomerization ; Arylcyanamide ; Ammonium Acetate ; Equeous Media ; Arylglyoxale