Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction
Abstract In this study, we report the synthesis of thieno[2,3‐c]pyridine derivatives by a metal‐free method via fused 1,2,3‐triazoles. In the synthesis of this skeleton using a three‐step method, we first obtained 1‐(2,2‐dimethoxyethyl)‐5‐(thiophen‐2‐yl)‐1H‐1,2,3‐triazole through a one‐pot triazolat...
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Wiley-VCH
2025-05-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202500060 |
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| author | Kumsal Eroğlu Prof. Dr. Ömer Tahir Günkara Prof. Dr. Wim Dehaen |
| author_facet | Kumsal Eroğlu Prof. Dr. Ömer Tahir Günkara Prof. Dr. Wim Dehaen |
| author_sort | Kumsal Eroğlu |
| collection | DOAJ |
| description | Abstract In this study, we report the synthesis of thieno[2,3‐c]pyridine derivatives by a metal‐free method via fused 1,2,3‐triazoles. In the synthesis of this skeleton using a three‐step method, we first obtained 1‐(2,2‐dimethoxyethyl)‐5‐(thiophen‐2‐yl)‐1H‐1,2,3‐triazole through a one‐pot triazolation reaction and in the next step, we synthesized the thieno[2,3‐c][1,2,3]triazolo[1,5‐ɑ]pyridine compound using a modified Pomeranz‐Fritsch reaction. In the final step, the synthesis of thieno[2,3‐c]pyridine derivatives was achieved in good yield via acid‐mediated denitrogenative transformation reactions. This mild condition synthetic process has enabled access to the title compounds, of which limited examples have been reported until now in the literature. Thus, the syntheses of 7‐(substituted methyl)thieno[2,3‐c]pyridine, thieno[2,3‐c]pyridine‐7‐ylmethyl esters, and imidazo[1,5‐ɑ]thieno[2,3‐c]pyridine derivatives have been successfully achieved. |
| format | Article |
| id | doaj-art-a4b5ad6ec8d14a23b09ed221edf9a2f9 |
| institution | Kabale University |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj-art-a4b5ad6ec8d14a23b09ed221edf9a2f92025-08-20T03:49:22ZengWiley-VCHChemistryOpen2191-13632025-05-01145n/an/a10.1002/open.202500060Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation ReactionKumsal Eroğlu0Prof. Dr. Ömer Tahir Günkara1Prof. Dr. Wim Dehaen2Department of Chemistry Yıldız Technical University Faculty of Art and Science Davutpasa Esenler 34220 Istanbul TürkiyeDepartment of Chemistry Yıldız Technical University Faculty of Art and Science Davutpasa Esenler 34220 Istanbul TürkiyeDepartment of Chemistry, KU Leuven Sustainable Chemistry for Metals and Molecules Celestijnenlaan 200F B-3001 Leuven BelgiumAbstract In this study, we report the synthesis of thieno[2,3‐c]pyridine derivatives by a metal‐free method via fused 1,2,3‐triazoles. In the synthesis of this skeleton using a three‐step method, we first obtained 1‐(2,2‐dimethoxyethyl)‐5‐(thiophen‐2‐yl)‐1H‐1,2,3‐triazole through a one‐pot triazolation reaction and in the next step, we synthesized the thieno[2,3‐c][1,2,3]triazolo[1,5‐ɑ]pyridine compound using a modified Pomeranz‐Fritsch reaction. In the final step, the synthesis of thieno[2,3‐c]pyridine derivatives was achieved in good yield via acid‐mediated denitrogenative transformation reactions. This mild condition synthetic process has enabled access to the title compounds, of which limited examples have been reported until now in the literature. Thus, the syntheses of 7‐(substituted methyl)thieno[2,3‐c]pyridine, thieno[2,3‐c]pyridine‐7‐ylmethyl esters, and imidazo[1,5‐ɑ]thieno[2,3‐c]pyridine derivatives have been successfully achieved.https://doi.org/10.1002/open.2025000601,2,3-triazolesmetal-free denitrogenative transformationthieno[2,3-c]pyridine |
| spellingShingle | Kumsal Eroğlu Prof. Dr. Ömer Tahir Günkara Prof. Dr. Wim Dehaen Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction ChemistryOpen 1,2,3-triazoles metal-free denitrogenative transformation thieno[2,3-c]pyridine |
| title | Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction |
| title_full | Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction |
| title_fullStr | Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction |
| title_full_unstemmed | Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction |
| title_short | Synthesis of Thieno[2,3‐c]pyridine Derivatives by 1,2,3‐Triazole‐Mediated Metal‐Free Denitrogenative Transformation Reaction |
| title_sort | synthesis of thieno 2 3 c pyridine derivatives by 1 2 3 triazole mediated metal free denitrogenative transformation reaction |
| topic | 1,2,3-triazoles metal-free denitrogenative transformation thieno[2,3-c]pyridine |
| url | https://doi.org/10.1002/open.202500060 |
| work_keys_str_mv | AT kumsaleroglu synthesisofthieno23cpyridinederivativesby123triazolemediatedmetalfreedenitrogenativetransformationreaction AT profdromertahirgunkara synthesisofthieno23cpyridinederivativesby123triazolemediatedmetalfreedenitrogenativetransformationreaction AT profdrwimdehaen synthesisofthieno23cpyridinederivativesby123triazolemediatedmetalfreedenitrogenativetransformationreaction |