New organoboron based multicomponent methodologies for the synthesis of novel heterocycles

• Main Author: Myslinska, Malgorzata
• Format: Dissertation
• Language: English
• Published: ProQuest Dissertations & Theses 01-01-2009
• Subjects: Organic chemistry; Pharmaceutical sciences
• ISBN: 9781109561937; 1109561938

This dissertation describes the development of new, efficient and facile synthetic methodologies for the practical synthesis of novel heterocycles and highly substituted amine derivatives. Chapter 1 is an introduction to the boron based multicomponent reaction known in the literature as the Petasis reaction. The reaction utilizes simple and easily available starting materials such as amines, carbonyls and organoboron compounds. This section describes the developments in the synthesis of heterocyclic scaffolds based on the three component Petasis reaction. Chapter 2 describes the use of potassium alkynyl trifluoroborates in the Petasis reaction for the synthesis of highly functionalized propargyl amine derivatives. Furthermore, it shows the utility of the propargylamines for the synthesis of heterocycles via the Pauson-Khand reaction and other palladium catalyzed transformations. Chapter 3 is an overview of existing methods for the indole synthesis. It presents a number of methodologies and discusses their utility and practicality. Chapter 4 introduces a novel, highly efficient and facile synthetic approach towards the synthesis of 2,3-disubstitued indoles. The new method utilizes an intramolecular cyclization of α-amino acids via a simple one pot transformation. The starting amino acids are synthesized via the three component Petasis reaction using 2-amino aryl ketones and a wide range of boronic acids. This method can be utilized for combinatorial library synthesis and has a potential to be used for the manufacture of pharmaceutically active ingredients. The section describes the synthesis of 2-amino aryl ketones as well. Chapter 5 provides details of the facile synthesis of fused novel heterocycles. A description of the three component condensation for the synthesis of á-amino acids derivatives of 2-amino heteroaryl ketones and their use in the construction of complex heterocyclic structures is presented. This section discusses utilization of the Gewald reaction for the synthesis of 2-amino heteroaryl ketones as well.* *Please refer to dissertation for diagrams.