Oral Presentation at Maryanoff Freshman Summer Research Symposium, Drexel University, October 5th 2017
"Anisyl Sulfanyl Methyl IsoCyanide (ASMIC): Rapid construction of Heterocyclic Scaffolds" by Maanasa Natrajan - Advisor, Dr. Fraser Fleming
We have recently developed a versatile isocyanide core, termed Anisyl Sulfanyl Methyl IsoCyanide (ASMIC), that allows for the formation of stable secondary carbanions upon deprotonation. Application of ASMIC to the synthesis of a broad spectrum of heterocycles has been realized through our preliminary investigations. Introduction of different electrophiles such as nitriles, ketones, and esters leads to the rapid formation of imidazole, oxazoline and oxazole containing scaffolds. In-situ trapping readily gives the N- protected analogs. These scaffolds also present several points for further modification via deprotonation/alkylations, exchange and coupling reactions. The anisyl sulfanyl group incorporates orthogonality to the scaffold by providing both nucleophilic and electrophilic behavior based on the type of applied modification.This method will be further explored for the rapid construction of other heterocyclic scaffolds such as imidazopyridines and thioimidazole pyridines.
"Anisyl Sulfanyl Methyl IsoCyanide (ASMIC): Rapid construction of Heterocyclic Scaffolds" by Maanasa Natrajan - Advisor, Dr. Fraser Fleming
We have recently developed a versatile isocyanide core, termed Anisyl Sulfanyl Methyl IsoCyanide (ASMIC), that allows for the formation of stable secondary carbanions upon deprotonation. Application of ASMIC to the synthesis of a broad spectrum of heterocycles has been realized through our preliminary investigations. Introduction of different electrophiles such as nitriles, ketones, and esters leads to the rapid formation of imidazole, oxazoline and oxazole containing scaffolds. In-situ trapping readily gives the N- protected analogs. These scaffolds also present several points for further modification via deprotonation/alkylations, exchange and coupling reactions. The anisyl sulfanyl group incorporates orthogonality to the scaffold by providing both nucleophilic and electrophilic behavior based on the type of applied modification.This method will be further explored for the rapid construction of other heterocyclic scaffolds such as imidazopyridines and thioimidazole pyridines.