期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 24, 页码 4555-4564出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200424
关键词
Cycloaddition; Nitrogen heterocycles; Sulfur heterocycles; Ylides
资金
- Deutsche Forschungsgemeinschaft
The N-alkylation of pyridines with cyanohydrin triflates or a-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.
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