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Synthesis 2021; 53(12): 2057-2066
DOI: 10.1055/a-1370-1884
DOI: 10.1055/a-1370-1884
paper
Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition
We are grateful to the Research Council of Tarbiat Modares University for support of this work.
Abstract
An ultrasound-promoted green protocol to access a new series of spirocyclopropanes from indeno[1,2-b]quinoxaline derivatives and azomethine ylides, generated in situ from the iodine-catalyzed reaction of acetophenones as well as of 2-methylquinoline with pyridine in the presence of a base, is described. These transformations proceed via a spirocyclopropanation reaction followed by elimination of pyridine. Clear evidence for the structure of a spirocyclopropane-linked indenoquinoxaline derivative was obtained from single-crystal X-ray analysis. The most important feature of this reaction is the fact it forms three stereogenic centers, one of which is quaternary, with excellent selectivity.
Key words
sonochemical synthesis - [3+2]-cycloaddition - spirocyclopropanes - azomethine ylides - iodineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1370-1884.
- Supporting Information
Publication History
Received: 30 July 2020
Accepted after revision: 22 January 2021
Accepted Manuscript online:
22 January 2021
Article published online:
15 February 2021
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