Issue 9, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
18 Jan 2019
Accepted
04 Mar 2019
First published
06 Mar 2019

Org. Chem. Front., 2019,6, 1428-1432

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, 6, 1428 DOI: 10.1039/C9QO00079H

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