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Ring Expansion Strategies for the Synthesis of Medium Sized Ring and Macrocyclic Sulfonamides. 2023

Zhongzhen Yang, and Illya Zalessky, and Ryan G Epton, and Adrian C Whitwood, and Jason M Lynam, and William P Unsworth
Department of Chemistry, University of York, York, YO10 5DD, UK.

Two new ring expansion strategies are reported for the synthesis of medium sized ring and macrocyclic sulfonamides. Both methods can be performed without using classical protecting groups, with the key ring expansion step initiated by nitro reduction and amine conjugate addition respectively. Each method can be used to make diversely functionalised cyclic sulfonamides in good to excellent yields, in a range of ring sizes. The ring size dependency of the synthetic reactions is in good agreement with the outcomes modelled by Density Functional Theory calculations.

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