One-Pot Preparation of (NH)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicar-boxylic Acids

11 November 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A one-pot transformation of biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives based on a Curtius rearrangement and subsequent basic hydrolysis was developed. This method is also applicable for the preparation of optically active amide-functionalized [7]helicene-like molecules. Furthermore, aza[5]helicene derivatives with a phosphate moiety were isolated as a product of the Curtius rearrangement step in the case of substrates that bear chalcogen atoms. The stereostructures of these products, revealed by X-ray diffraction analysis, suggested that chalcogen-bonding and pnictogen-bonding interactions might contribute to their stabilization. The configurational stability of the helicene-like molecules and their chiroptical properties were further investigated.

Keywords

lactamization
Curtius rearrangement
phenanthridinone
helicene-like molecule

Supplementary materials

Title
Description
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Title
SI-1
Description
Experimental procedure, spectroscopic, and HPLC data
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Title
SI-2
Description
NMR spectra
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