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DOI: 10.1055/a-1731-9464
FeCl3-Promoted Facile Synthesis of Multiply Arylated Nicotinonitriles
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Abstract
Many biologically active nicotinonitriles have been reported to date. Consequently, the development of synthetic methods for multiply arylated/alkylated nicotinonitriles remains a sought-after field of research. In the present work, a new synthetic strategy for multi-substituted nicotinonitriles is described. A FeCl3-promoted condensation–cyclization reaction of an enamino nitrile and α,β-unsaturated ketones proceeded efficiently with a wide range of substrates. It is noteworthy that this method facilitates access to fully and differently substituted nicotinonitriles, including tetra-arylated nicotinonitriles, in only three steps. Using the functionality of the cyano group, the copper-catalyzed annulation reaction of the nicotinonitrile was achieved to yield benzo[c][2,7]naphthyridin-5(6H)-one.
Key words
polysubstituted nicotinonitrile - iron(III) chloride - enamino nitrile - α,β-unsaturated ketoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1731-9464.
- Supporting Information
Publication History
Received: 09 December 2021
Accepted after revision: 05 January 2022
Accepted Manuscript online:
05 January 2022
Article published online:
09 February 2022
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