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RESEARCH PRODUCT
A Modular Synthesis of Polysubstituted Indolizines
Till OpatzMurat Kucukdislisubject
Bromoacetonitrilechemistry.chemical_compoundchemistryOrganic ChemistryPyridineOrganic chemistryNitroalkaneIndolizinePyridiniumPhysical and Theoretical ChemistryCycloadditionCyanohydrindescription
The N-alkylation of pyridines with cyanohydrin triflates or α-halonitriles furnishes 1-(1-cyanoalkyl)pyridinium salts that can react with nitroolefins under basic conditions to furnish polysubstituted indolizines. Overall, the indolizine core can be constructed from a pyridine, two aldehydes, and a nitroalkane, and no undesired functional groups remain in the products. When bromoacetonitrile was used for the N-alkylation, indolizine-3-carbonitriles were obtained instead. The pyridine component may be replaced by other azines, giving rise to related heterocyclic systems.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-07-04 | European Journal of Organic Chemistry |