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Synthesis 2019; 51(12): 2548-2552
DOI: 10.1055/s-0037-1611532
DOI: 10.1055/s-0037-1611532
paper
Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines
We thank the California Institute for Regenerative Medicine (CIRM) program at UCLA for support.Further Information
Publication History
Received: 07 March 2019
Accepted after revision: 10 April 2019
Publication Date:
02 May 2019 (online)
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Abstract
Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N-methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611532.
- Supporting Information
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References
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The formation of this anion is precedented in the literature: