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Updated: Jul 14, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Deaminative ring contraction for the synthesis of polycyclic heteroaromatics: a concise total synthesis of
Emily K Kirkeby1, Zachary T Schwartz1, Myles A Lovasz1
1Department of Chemistry, University of Utah 315 South 1400 East Salt Lake City Utah 84112 USA roberts@chem.utah.edu.
Abstract:
A concise strategy to prepare polycyclic heteroaromatics involving a deaminative contraction cascade is detailed. The efficient deaminative ring contraction involves the in situ methylation of a biaryl-linked dihydroazepine to form a cyclic ammonium cation that undergoes a base-induced [1,2]-Stevens rearrangement/dehydroamination sequence. The presence of pseudosymmetry guides the retrosynthetic analysis of pyridyl-containing polycyclic heteroaromatics, enabling their construction by the reductive cyclization and deaminative contraction of tertiary amine precursors.
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