Manganese Complex Catalyzed Sequential Multi‐component Reaction: Enroute to a Quinoline‐Derived Azafluorenes

Abstract

AbstractThe development of innovative synthetic strategies for constructing complex molecular structures is the heart of organic chemistry. This significance of novel reactions or reaction sequences would further enhance if they permitted the synthesis of new classes of structural motifs, which have not been previously created. The research on the synthesis of heterocyclic compounds is one of the most active topics in organic chemistry due to the widespread application of N‐heterocycles in life and material science. The development of a new catalytic process that employs first‐row transition metals to produce a range of heterocycles from renewable raw materials is considered highly sustainable approach. This would be more advantageous if done in an eco‐friendly and atom‐efficient manner. Herein we introduce, the synthesis of various new quinoline based azafluorenes via sequential dehydrogenative multicomponent reaction (MCR) followed by C(sp3)−H hydroxylation and annulation. Our newly developed, Mn‐complexes have the ability to direct the reaction in order to achieve a high amount of desired functionalized heterocycles while minimizing the possibility of multiple side reactions. We also performed a series of control experiments, hydride trapping experiments, reaction kinetics, catalytic intermediate and DFT studies to comprehend the detailed reaction route and the catalyst‘s function in the MCR sequence.