Synlett 2022; 33(19): 1907-1912
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

Gciniwe S. Mathenjwa
a   School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, 3209, South Africa
,
Matthew P. Akerman
a   School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, 3209, South Africa
,
b   Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050, Johannesburg, South Africa
,
c   Department of Chemistry, University of Cape Town, Rondebosch, Cape Town, 7700, South Africa
› Institutsangaben

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.


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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.

Supporting Information



Publikationsverlauf

Eingereicht: 14. April 2022

Angenommen nach Revision: 07. Juli 2022

Accepted Manuscript online:
07. Juli 2022

Artikel online veröffentlicht:
05. August 2022

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