Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction
Abstract Indole derivatives substituted at the C‐2 position have shown important biological activities. Due to these properties, several methods have been described for the preparation of structurally diverse indoles. In this work, we have synthesized highly functionalized indole derivatives via Rh(...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2023-06-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202300070 |
| _version_ | 1797763842443313152 |
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| author | Marcelo Augusto Pereira Januário Demetrius P. deSouza Prof. Dr. Julio Zukerman‐Schpector Prof. Dr. Arlene G. Corrêa |
| author_facet | Marcelo Augusto Pereira Januário Demetrius P. deSouza Prof. Dr. Julio Zukerman‐Schpector Prof. Dr. Arlene G. Corrêa |
| author_sort | Marcelo Augusto Pereira Januário |
| collection | DOAJ |
| description | Abstract Indole derivatives substituted at the C‐2 position have shown important biological activities. Due to these properties, several methods have been described for the preparation of structurally diverse indoles. In this work, we have synthesized highly functionalized indole derivatives via Rh(III)‐catalyzed C‐2 alkylation with nitroolefins. Under the optimized condition, 23 examples were prepared with 39–80 % yield. Moreover, the nitro compounds were reduced and submitted to the Ugi four‐component reaction, furnishing a series of new indole‐peptidomimetics in moderate to good overall yields. |
| first_indexed | 2024-03-12T19:48:06Z |
| format | Article |
| id | doaj.art-5a7ebe735aae4f92b3d336e282373cbb |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-03-12T19:48:06Z |
| publishDate | 2023-06-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-5a7ebe735aae4f92b3d336e282373cbb2023-08-02T03:25:33ZengWiley-VCHChemistryOpen2191-13632023-06-01126n/an/a10.1002/open.202300070Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi ReactionMarcelo Augusto Pereira Januário0Demetrius P. deSouza1Prof. Dr. Julio Zukerman‐Schpector2Prof. Dr. Arlene G. Corrêa3Centre of Excellence for Research in Sustainable Chemistry Department of Chemistry Federal University of São Carlos 13565-905 São Carlos – SP BrazilCentre of Excellence for Research in Sustainable Chemistry Department of Chemistry Federal University of São Carlos 13565-905 São Carlos – SP BrazilDepartment of Chemistry Federal University of São Carlos 13565-905 São Carlos – SP BrazilCentre of Excellence for Research in Sustainable Chemistry Department of Chemistry Federal University of São Carlos 13565-905 São Carlos – SP BrazilAbstract Indole derivatives substituted at the C‐2 position have shown important biological activities. Due to these properties, several methods have been described for the preparation of structurally diverse indoles. In this work, we have synthesized highly functionalized indole derivatives via Rh(III)‐catalyzed C‐2 alkylation with nitroolefins. Under the optimized condition, 23 examples were prepared with 39–80 % yield. Moreover, the nitro compounds were reduced and submitted to the Ugi four‐component reaction, furnishing a series of new indole‐peptidomimetics in moderate to good overall yields.https://doi.org/10.1002/open.202300070CH activationindoleRh catalysisnitroalkane reductionUgi reaction |
| spellingShingle | Marcelo Augusto Pereira Januário Demetrius P. deSouza Prof. Dr. Julio Zukerman‐Schpector Prof. Dr. Arlene G. Corrêa Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction ChemistryOpen CH activation indole Rh catalysis nitroalkane reduction Ugi reaction |
| title | Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction |
| title_full | Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction |
| title_fullStr | Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction |
| title_full_unstemmed | Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction |
| title_short | Rh(III)‐Catalyzed C‐2 Alkylation of Indoles followed by a Post‐Synthetic Modification via the Ugi Reaction |
| title_sort | rh iii catalyzed c 2 alkylation of indoles followed by a post synthetic modification via the ugi reaction |
| topic | CH activation indole Rh catalysis nitroalkane reduction Ugi reaction |
| url | https://doi.org/10.1002/open.202300070 |
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