Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines
A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.17.42 |
| _version_ | 1819143545320112128 |
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| author | Geetanjali S. Sontakke Rahul K. Shukla Chandra M. R. Volla |
| author_facet | Geetanjali S. Sontakke Rahul K. Shukla Chandra M. R. Volla |
| author_sort | Geetanjali S. Sontakke |
| collection | DOAJ |
| description | A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products. |
| first_indexed | 2024-12-22T12:27:57Z |
| format | Article |
| id | doaj.art-fc76a2ce3658458f8dd71918b5bbc254 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T12:27:57Z |
| publishDate | 2021-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-fc76a2ce3658458f8dd71918b5bbc2542022-12-21T18:25:45ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-02-0117148549310.3762/bjoc.17.421860-5397-17-42Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolinesGeetanjali S. Sontakke0Rahul K. Shukla1Chandra M. R. Volla2Department of Chemistry, Indian Institute of Technology Bombay, Powai-400076, Mumbai, IndiaDepartment of Chemistry, Indian Institute of Technology Bombay, Powai-400076, Mumbai, IndiaDepartment of Chemistry, Indian Institute of Technology Bombay, Powai-400076, Mumbai, IndiaA metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.https://doi.org/10.3762/bjoc.17.42aminationheteroarylationquinoline n-oxidesregioselectivetriazoles |
| spellingShingle | Geetanjali S. Sontakke Rahul K. Shukla Chandra M. R. Volla Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines Beilstein Journal of Organic Chemistry amination heteroarylation quinoline n-oxides regioselective triazoles |
| title | Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines |
| title_full | Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines |
| title_fullStr | Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines |
| title_full_unstemmed | Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines |
| title_short | Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines |
| title_sort | deoxygenative c2 heteroarylation of quinoline n oxides facile access to α triazolylquinolines |
| topic | amination heteroarylation quinoline n-oxides regioselective triazoles |
| url | https://doi.org/10.3762/bjoc.17.42 |
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