Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium
Farhad Golmohammadi1, Chiman Osmani1, Frank Rominger2
1Peptide Chemistry Research Institute, K. N. Toosi University Of Technology, P.O. Box 15875-4416 Tehran 19697, Iran.
Abstract:
A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- and oxidant-free [3 + 2] cycloaddition reaction of zwitterionic ketenimines and pyridinium salts. This versatile method proceeds under mild conditions, affording functionalized indolizines in moderate to good yields. This efficient approach involves an intermolecular [3 + 2] cycloaddition, followed by enamine/imine tautomerization and aromatization. Notably, this method demonstrates broad functional group compatibility and allows for facile scalability, making it a valuable tool for the synthesis of indolizine-based frameworks in organic and medicinal chemistry.
More Related Videos
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
α-Alkylation of Ketones via Enolate Ions
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
