Application of Transition-Metal-Catalyzed Reactions for the Construction of Polycycles, Cyclophanes, and Ferrocene-Based Macrocycles
Implementing Organization
K.T.H.M. College, Nashik, Maharashtra
Principal Investigator
Dr. Milind Pandurang Meshram
K.T.H.M. College, Nashik, Maharashtra
Project Overview
The study aims to synthesize important molecules like polycycles, macrocycles, and cyclophanes using transition metal-catalyzed reactions. The goal is to develop efficient and atom-economical methods using environmentally benign and less expensive catalysts like FeCl3. The iron-catalyzed carbonyl-alkyne-metathesis and carbonyl-olefin metathesis reactions are particularly efficient for making C=C bonds. The ferrocene skeleton is identified as an important unit in the synthetic sequences, with simple ferrocene derivatives acting as key building blocks for functionalization using transition-metal-catalyzed reactions like Heck, Sonogashira, Suzuki–Miyaura cross-coupling reactions, and Buchwald‒Hartwig coupling. The resulting key precursors will be studied in Lewis acid-catalyzed ring-closing carbonyl-alkyne-metathesis, ring-closing carbonyl-olefin metathesis, and base-mediated carbonyl-allene metathesis reactions for the generation of various polycyclic and macrocyclic frameworks. The newly generated ferrocene-based macrocycles can be used for SAR studies due to their medicinal use. The study also explores the formation of functionalized β-carboline analogs, starting with the corresponding bromo/iodo derivatives. The halogen-containing β-carboline derivatives are used as building blocks for functionalizing them using transition-metal-catalyzed reactions. The resulting key precursors can be used in Lewis acid-catalyzed ring-closing carbonyl-alkyne-metathesis, carbonyl-olefin metathesis, and base-mediated carbonyl-allene metathesis reactions for the construction of higher analogs of β-carboline. Higher analogs of β-carboline can deliver "drug-like" molecules, which can be used for SAR studies.