β-carbolines, or pyrido[3,4-<i>b</i>]indoles, are a class of molecules with wide-ranging biological activity. The synthesis of b-carbolines is a mature field, yet new methods are desirable to introduce new functionality onto the core scaffold. We will describe two novel methods of synthesizing unnatural β–carbolines bearing an annulation at the 3,4-position: First, we will describe a five-step synthesis in which we will vary the constitution of an alkynyl nitrile linker. Second, we will describe a novel palladium-catalyzed, one-pot Sonogashira coupling/intramolecular [2+2+2] cyclization towards these structures. This method produces a novel tetrahydropyrrolo-annulated β-carboline in 80% yield. Further, the effects of constitutionally unique linkers on this one-pot reaction on proximity of the pendant nitrile in the [2+2+2] cyclization will be described.

Palladium-catalyzed one-pot reactions towards β-carbolines

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.