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Issue 56, 2015
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Double functionalization of 2-amino-2′-hydroxy-1,1′-biaryls: synthesis of 4-nitro-dibenzofurans and benzofuro-indoles

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Abstract

Several substituted 2′-amino-biphenyl-2-ols were synthesized. The mild and TM-free double functionalization: nitration and cycloetherification of 2′-amino-biphenyl-2-ols have been achieved for the synthesis of functionalized 4-nitro-dibenzofurans utilizing NaNO2 in TFA and water. Interestingly, nitration of phenol ring was observed along with the dibenzofuran ring formation in the one-pot synthesis. The position of the nitro group in several dibenzofurans is also established by X-ray crystal structure studies. Further functionalization of the obtained 4-nitro-dibenzofurans has been carried into 3-nitro-terphenyl-2-ol, novel benzofuro-indoles, and amino-dibenzofurans. The mechanistic understanding on double functionalization of 2′-amino-biphenyl-2-ols suggests that reaction proceeds by a combination of nitration of the phenol ring followed by Sandmeyer reaction for dibenzofuran ring formation.

Graphical abstract: Double functionalization of 2-amino-2′-hydroxy-1,1′-biaryls: synthesis of 4-nitro-dibenzofurans and benzofuro-indoles

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Publication details

The article was received on 15 Mar 2015, accepted on 27 Apr 2015 and first published on 28 Apr 2015


Article type: Paper
DOI: 10.1039/C5RA07328F
Citation: RSC Adv., 2015,5, 44728-44741
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    Double functionalization of 2-amino-2′-hydroxy-1,1′-biaryls: synthesis of 4-nitro-dibenzofurans and benzofuro-indoles

    A. Kumar, Moh. Sattar, A. Verma, A. Dara and S. Kumar, RSC Adv., 2015, 5, 44728
    DOI: 10.1039/C5RA07328F

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