Synthetic and Mechanistic Investigation of an Unexpected ­Intramolecular 1-5 Nitrogen to Carbon Tosyl Migration

Abstract

Controlled sulfonyl migration is considered an important transformation for total synthesis and scaffold elaboration. Accordingly, efforts to understand the underlying properties of these often serendipitously identified reactions have important implications. Following the attempted synthesis of a tetrahydroindazolone analogue, we report here an unexpected 1,5-nitrogen to carbon tosyl migration, resulting in the isolation of an unusual sulfonated dimedone. Synthetic and mechanistic investigations provide early insight into the scope of this reaction, with two potential mechanisms proposed.

Key words

sulfonyl migration - tosyl hydrazone - tetrahydroindazolone - pyrazolidinones - HSP90 inhibitors

Publication History

Received: 14 April 2022

Accepted after revision: 07 July 2022

Accepted Manuscript online:
07 July 2022

Article published online:
05 August 2022

• References and Notes

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