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Student Research Projects

Conjugate Addition of Active Methylene Carbon Nucleophiles to Quinoline Vinylacetylines: New Access to the Synthesis of Highly Functionalized Benzoindolizines

Student Rachel A Francher
Faculty Mentor(s) Dr. Anthony Hayford
Department Chemistry
Course CHEM 489: Research in the Natural Sciences

Abstract

Benzoindolizines are a class of heterocyclic compounds that have several medicinal applications in the area of pharmaceuticals. The synthesis of benzoindolizines can be used for the production of therapeutic drugs for tuberculosis and some types of cancers. One common method for synthesizing benzoindolizines is the 1, 3 dipolar cycloaddition of ylides. In our research, we have successfully used the 1, 6 conjugate (Michael) addition to combine methylene carbanions with quinoline vinylacetylines to produce benzoindolizines. Various methylene carbanions such as malononitrile and ethyl cyanoacetate have yielded simple analogues of highly functionalized benzoindolizines when added to the silyated quinoline.

 

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