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Issue 32, 2018
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Molecular diversity of the domino annulation reaction of 2-aryl-3-nitrochromenes with pivaloylacetonitriles

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Abstract

In the presence of triethylamine, the domino annulation reaction of two molecules of pivaloylacetonitrile with one molecule of 2-aryl-3-nitrochromene in tetrahydrofuran resulted in the unprecedented imino-substituted dihydrofuro[2,3-c]chromene derivatives in high yields. More importantly, the above domino reaction in refluxing methanol or ethanol afforded alkoxy-substituted chromeno[3,4-b]pyridines in satisfactory yields. However, a similar reaction of benzoylacetonitrile with 2-aryl-3-nitrochromenes in basic medium gave the expected furo[2,3-c]chromene derivatives in moderate yields.

Graphical abstract: Molecular diversity of the domino annulation reaction of 2-aryl-3-nitrochromenes with pivaloylacetonitriles

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Supplementary files

Article information


Submitted
26 Jun 2018
Accepted
24 Jul 2018
First published
25 Jul 2018

Org. Biomol. Chem., 2018,16, 5816-5822
Article type
Paper

Molecular diversity of the domino annulation reaction of 2-aryl-3-nitrochromenes with pivaloylacetonitriles

W. Jiang, J. Sun, R. Liu and C. Yan, Org. Biomol. Chem., 2018, 16, 5816
DOI: 10.1039/C8OB01504J

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