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Triphenyiphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls: A Practical and Convenient Synthesis of Carbazoles.

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Title: Triphenyiphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls: A Practical and Convenient Synthesis of Carbazoles.
Authors: Freeman, Adam W.1 adam.freeman@kodak.com, Urvoy, Marie1, Criswell, Megan E.1
Source: Journal of Organic Chemistry. 6/24/2005, Vol. 70 Issue 13, p5014-5019. 6p. 4 Diagrams, 3 Charts.
Subjects: Solvents, Solution (Chemistry), Organic chemistry, Chemical reactions, Ring formation (Chemistry)
Abstract: The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 17496886
AccessLevel: 6
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  Data: Triphenyiphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls: A Practical and Convenient Synthesis of Carbazoles.
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  Data: <searchLink fieldCode="AR" term="%22Freeman%2C+Adam+W%2E%22">Freeman, Adam W.</searchLink><relatesTo>1</relatesTo><i> adam.freeman@kodak.com</i><br /><searchLink fieldCode="AR" term="%22Urvoy%2C+Marie%22">Urvoy, Marie</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Criswell%2C+Megan+E%2E%22">Criswell, Megan E.</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 6/24/2005, Vol. 70 Issue 13, p5014-5019. 6p. 4 Diagrams, 3 Charts.
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  Data: <searchLink fieldCode="DE" term="%22Solvents%22">Solvents</searchLink><br /><searchLink fieldCode="DE" term="%22Solution+%28Chemistry%29%22">Solution (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+chemistry%22">Organic chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink>
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  Data: The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/jo0503299
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        Text: English
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        Type: general
      – SubjectFull: Solution (Chemistry)
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      – SubjectFull: Organic chemistry
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      – SubjectFull: Chemical reactions
        Type: general
      – SubjectFull: Ring formation (Chemistry)
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      – TitleFull: Triphenyiphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls: A Practical and Convenient Synthesis of Carbazoles.
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              Text: 6/24/2005
              Type: published
              Y: 2005
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