Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine
Indeno[1,2⁃d]pyridazine derivatives have wide applications in pesticides,pharmaceuticals,and other fields due to their excellent biological activities.Therefore,the development of rapid and efficient synthetic methods for these compounds has attracted increasing attention from researchers.A novel ac...
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| Format: | Article |
| Language: | zho |
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Editorial Department of Journal of Petrochemical Universities
2025-04-01
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| Series: | Shiyou huagong gaodeng xuexiao xuebao |
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| Online Access: | https://journal.lnpu.edu.cn/syhg/CN/10.12422/j.issn.1006-396X.2025.02.008 |
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| author | Wenqing LIU He WANG Xin WANG Lei LI |
| author_facet | Wenqing LIU He WANG Xin WANG Lei LI |
| author_sort | Wenqing LIU |
| collection | DOAJ |
| description | Indeno[1,2⁃d]pyridazine derivatives have wide applications in pesticides,pharmaceuticals,and other fields due to their excellent biological activities.Therefore,the development of rapid and efficient synthetic methods for these compounds has attracted increasing attention from researchers.A novel acid⁃catalyzed cyclization reaction between allylbenzene and tetrazine was designed.Reaction intermediates were trapped,and their structures,along with those of the products,were characterized using nuclear magnetic resonance spectroscopy.The results indicate that the reaction proceeds through intermolecular [4+2] cycloaddition and intramolecular Friedel⁃Crafts alkylation processes,enabling one⁃step synthesis of indeno[1,2⁃d]pyridazine derivatives.The reaction also exhibits a broad substrate scope and good functional group compatibility,yielding a series of indeno[1,2⁃d]pyridazine derivatives with 67%~95% yields.In gram scale experiments,the target product was obtained with an 81% yield, demonstrating the potential practical value of this reaction. |
| format | Article |
| id | doaj-art-cd70f4b285bc4f139c8586bbe0dec78c |
| institution | DOAJ |
| issn | 1006-396X |
| language | zho |
| publishDate | 2025-04-01 |
| publisher | Editorial Department of Journal of Petrochemical Universities |
| record_format | Article |
| series | Shiyou huagong gaodeng xuexiao xuebao |
| spelling | doaj-art-cd70f4b285bc4f139c8586bbe0dec78c2025-08-20T02:43:28ZzhoEditorial Department of Journal of Petrochemical UniversitiesShiyou huagong gaodeng xuexiao xuebao1006-396X2025-04-01382627110.12422/j.issn.1006-396X.2025.02.008Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and TetrazineWenqing LIU0He WANG1Xin WANG2Lei LI3School of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning 113001，ChinaSchool of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning 113001，ChinaSchool of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning 113001，ChinaSchool of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning 113001，ChinaIndeno[1,2⁃d]pyridazine derivatives have wide applications in pesticides,pharmaceuticals,and other fields due to their excellent biological activities.Therefore,the development of rapid and efficient synthetic methods for these compounds has attracted increasing attention from researchers.A novel acid⁃catalyzed cyclization reaction between allylbenzene and tetrazine was designed.Reaction intermediates were trapped,and their structures,along with those of the products,were characterized using nuclear magnetic resonance spectroscopy.The results indicate that the reaction proceeds through intermolecular [4+2] cycloaddition and intramolecular Friedel⁃Crafts alkylation processes,enabling one⁃step synthesis of indeno[1,2⁃d]pyridazine derivatives.The reaction also exhibits a broad substrate scope and good functional group compatibility,yielding a series of indeno[1,2⁃d]pyridazine derivatives with 67%~95% yields.In gram scale experiments,the target product was obtained with an 81% yield, demonstrating the potential practical value of this reaction.https://journal.lnpu.edu.cn/syhg/CN/10.12422/j.issn.1006-396X.2025.02.008allylbenzenesindeno[12⁃d]pyridazine derivatives[4+2] cycloadditionfriedel⁃crafts reaction |
| spellingShingle | Wenqing LIU He WANG Xin WANG Lei LI Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine Shiyou huagong gaodeng xuexiao xuebao allylbenzenes indeno[1 2⁃d]pyridazine derivatives [4+2] cycloaddition friedel⁃crafts reaction |
| title | Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine |
| title_full | Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine |
| title_fullStr | Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine |
| title_full_unstemmed | Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine |
| title_short | Study on the Acid⁃Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine |
| title_sort | study on the acid⁃catalyzed cyclization reaction of allylbenzenes and tetrazine |
| topic | allylbenzenes indeno[1 2⁃d]pyridazine derivatives [4+2] cycloaddition friedel⁃crafts reaction |
| url | https://journal.lnpu.edu.cn/syhg/CN/10.12422/j.issn.1006-396X.2025.02.008 |
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