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Convenient construction of dibenzo[b,d]furanes and 2,6-diaryl-4-(2-hydroxyphenyl)pyridines via domino reaction of pyridinium ylides with 2-aryl-3-nitrochromenes

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Abstract

The DBU promoted domino annulation reaction of 2-aryl-3-nitrochromenes with two molecular 4-(N,N-dimethylamino)-1-phenacylpyridinium bromides in DMF resulted in unprecedented 1-benzoyl-2,4-diaryldibenzo[b,d]furane derivatives in good yields, in which the six-membered pyran ring was readily converted to the five-membered furan ring. On the other hand, the three-component reaction of ammonium acetate, 2-aryl-3-nitrochromenes and 4-(N,N-dimethylamino)-1-phenacylpyridinium bromides in refluxing ethanol afforded 2,6-diaryl-4-(2-hydroxyphenyl)pyridines in high yields.

Graphical abstract: Convenient construction of dibenzo[b,d]furanes and 2,6-diaryl-4-(2-hydroxyphenyl)pyridines via domino reaction of pyridinium ylides with 2-aryl-3-nitrochromenes

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Publication details

The article was received on 18 Jan 2019, accepted on 04 Mar 2019 and first published on 06 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00079H
Citation: Org. Chem. Front., 2019, Advance Article

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    Convenient construction of dibenzo[b,d]furanes and 2,6-diaryl-4-(2-hydroxyphenyl)pyridines via domino reaction of pyridinium ylides with 2-aryl-3-nitrochromenes

    J. Sun, W. Jiang and C. Yan, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00079H

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