Pyrido[3,4-b]indoles are small heterocycles that are important modulators of biological processes. We have been interested in new ways to use transition metal catalysis in synthesis, and have identified an intramolecular [2+2+2] cyclization as a convenient way to prepare these structures. We will describe a five--step synthesis in which we will vary the substitution pattern on the aniline ring prior to cyclization in order to determine its effect on overall yield and reaction rate. These ortho-, meta-, and para-substituted functional groups are wide-ranging and demonstrate the wide substrate scope of this reaction. Finally, we will describe a one-pot Pd-catalyzed variant of this reaction that reduces the number of steps in the sequence.

Synthesis of differentially substituted pyrido[3,4-b]indoles by Rh(I)-catalysis

255th National Meeting (2018)

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