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Synthesis 2021; 53(12): 2081-2091
DOI: 10.1055/s-0040-1706660
DOI: 10.1055/s-0040-1706660
paper
A Cascade Process of Hydroxamates Renders 1,6-Dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones
The authors are grateful for financial support from Monash University through the award of a Ph.D. scholarship to Z.N.
Abstract
A cascade route to 1,6-dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones from N,O-diacyl hydroxylamines consisting of a two-step procedure is described. The key transformation is a [3,3]-sigmatropic rearrangement of N,O-diacyl hydroxylamines promoted by formation of a silylketenaminal followed by an intramolecular cyclization and a final spirocyclization. The optimum reaction conditions employ a one-fold excess of each reagent and are utilized to prepare a range of structurally diverse examples of this class of compound.
Key words
[3,3]-sigmatropic rearrangement - cascade process - N,O-diacyl hydroxylamines - 3-azaspirocyclic orthoamides - 1,6-dioxa-3,9-diazaspiro[4.4]nonane-2,8-dionesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706660.
- Supporting Information
Publication History
Received: 29 October 2020
Accepted after revision: 08 December 2020
Article published online:
19 January 2021
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