SYNTHESIS OF BIOACTIVE MOLECULES BY METAL AND NON-METAL CATALYSIS

• Main Authors: DONALA JANREDDY, 瑞迪
• Other Authors: Ching-Fa Yao
• Format: Others
• Language: en_US
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/13128064128379464074

博士 === 國立臺灣師範大學 === 化學系 === 102 === The content of this dissertation is divided into three parts. The part I is subdivided into three sections. Section A, illustrate the overview, classification and synthetic approaches on ‘indole nucleus’ reactions and related literature review. Section B demonstrate the ‘An Easy Access to Carbazolones and 2,3-Disubstituted Indoles’ by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones. Section C, describes the synthesis of ‘2,3-disubstituted indoles’ via cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2. Part II deals with the synthesis of 2-aryl benzoxazole derivatives and 1,2,3-triazoles by using transition metal catalyzed reactions. Part II is subdivided into three sections. Section A, deals with overview, classification and synthetic approaches of 2-aryl benzoxazole derivatives. This section also describe the overview on 1,2,3- triazole derivatives, classification and synthetic approaches from azide and alkenes. Section B, represents an efficient synthesis of 2-aryl benzoxazole derivatives having an amine or amide functionality in the aryl group at the ortho position via Copper-catalyzed tandem C–N and C–O bond formation. Section C, deals with the novel synthesis of substituted 1,2,3-triazoles via Copper(I)-catalyzed aerobic oxidative azide–alkene cycloaddition. Part III deals with the synthesis of naphthalene by using non-metal, transition metal catalyzed reactions and their application towards diversity oriented synthesis. Part III is subdivided into three sections. Section A, deals with overview and synthetic approaches towards naphthalene derivatives. Section B, describes an efficient synthesis of naphthalenes and iodo-substituted isochromene derivatives via reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts using molecular iodine. The resulting iodo-substituted-derivatives utilized to couple with a array of boronic acid (Suzuki coupling), activated alkene (Heck coupling) and alkyne (Sonogashira reaction). Section C, demonstrates an efficient synthesis of naphthalenes via PdCl2-catalyzed aerobic oxidative intermolecular cycloaddition between 2-alkenyl benzaldehydes and electron-deficient terminal alkenes.