Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo-Diaza-Cope Rearrangement
We disclose a new Br?nsted acid promoted quinoline synthesis, proceeding via homo-diaza-Cope rearrangement of N-aryl-N′-cyclopropyl hydrazines. Our strategy can be considered a homologation of Fischer's classical indole synthesis and delivers 6-membered N-heterocycles, including previously inaccessible pyridine derivatives. This approach can also be used as a pyridannulation methodology toward constructing polycyclic polyheteroaromatics. A computational analysis has been employed to probe plausible activation modes and to interrogate the role of the catalyst.
De, Chandra Kanta,Gerosa, Gabriela Guillermina,List, Benjamin,Maji, Rajat,Schwengers, Sebastian Armin
