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Synlett 2022; 33(19): 1907-1912
DOI: 10.1055/a-1893-7550
DOI: 10.1055/a-1893-7550
letter
Thieme Chemistry Journals Awardees 2022
Synthetic and Mechanistic Investigation of an Unexpected Intramolecular 1-5 Nitrogen to Carbon Tosyl Migration
The authors acknowledge support from the National Research Foundation of South Africa (NRF, Grant No. 116305) and Future Leaders – African Independent Research (FLAIR), a partnership between the African Academy of Sciences and the Royal Society that is funded by the UK Government as part of the Global Challenges Research Fund (GCRF). GSM gratefully acknowledges financial support from the NRF.
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 inhibitorsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1893-7550.
- Supporting Information
Publication History
Received: 14 April 2022
Accepted after revision: 07 July 2022
Accepted Manuscript online:
07 July 2022
Article published online:
05 August 2022
© 2022. Thieme. All rights reserved
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