Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones

Scholarly Works

• Niu, Y.-N.; Wang, K.-Y.; Han, F.-Y.; Xia, X.-F. Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides. Tetrahedron 2025, 174, 134497. doi:10.1016/j.tet.2025.134497
• Zhang, T.; Ren, X.; Li, J.; Wang, Y.; Wang, B.; Chen, Z.; Xia, Y.; Wu, S.; Liu, C.; Zhang, Y. Lewis Acidic Ionic-Liquid-Catalyzed Radical-Cascade Alkylation/Cyclization of N-Alkyl-N-methacryloyl Benzamides with Alkanes via Visible-Light-Induced Ligand-to-Metal Charge Transfer: Access to Alkylated Isoquinoline-1,3(2H,4H)-diones. Organic letters 2024, 26, 10259–10266. doi:10.1021/acs.orglett.4c03697
• Li, D.; Zhu, X.; zhao, H.; Hao, X.; Wu, Y. Synthesis of bistricyclic aromatic enes and related polycyclic systems via Pd-catalyzed tandem Suzuki coupling/Heck cyclization reaction. Tetrahedron Letters 2024, 150, 155297. doi:10.1016/j.tetlet.2024.155297
• Ren, X.; Zhang, T.; Wang, B.; Jin, W.; Xia, Y.; Wu, S.; Liu, C.; Zhang, Y. Visible-Light-Driven Bifunctional Photocatalytic Radical-Cascade Selenocyanation/Cyclization of Acrylamides with KSeCN. The Journal of organic chemistry 2024, 89, 5783–5796. doi:10.1021/acs.joc.4c00362
• Li, Q.; Zhu, Z.-Q.; Zhang, W.-Y.; Le, Z.-G.; Xie, Z.-B. Visible-light-induced decarboxylative cascade cyclization of acryloylbenzamides with N-hydroxyphthalimide esters via EDA complexes. Organic & biomolecular chemistry 2024, 22, 965–969. doi:10.1039/d3ob01970e
• Arora, S.; Singh, T.; Mondal, U.; Singh, A. Visible Light Mediated Halogen Atom Transfer to Access Polyhalogenated and Deuterated Lactams from Alkyl Halides. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300469
• Niu, Y.-N.; Xia, X.-F. Recent developments in the synthesis of the isoquinoline-1,3(2H,4H)-dione by radical cascade reaction. Organic & biomolecular chemistry 2022, 20, 7861–7885. doi:10.1039/d2ob01554d
• Li, J.-Z.; Mei, L.; Yu, X.-C.; Wang, L.-T.; Cai, X.-E.; Li, T.; Wei, W.-T. C-centered radical-initiated cyclization by directed C(sp3)–H oxidative functionalization. Organic Chemistry Frontiers 2022, 9, 5726–5757. doi:10.1039/d2qo01128j
• Li, J.; Mei, L.; Cai, X.; Zhang, C.; Cao, T.; Huang, X.; Liu, Y.; Wei, W. Transition‐Metal‐Free Radical Cyclization of 2‐Arylbenzoimidazoles with Unactivated AlkanesviaC(sp3)−H Functionalizations in Aqueous Media. Advanced Synthesis & Catalysis 2022, 364, 2080–2085. doi:10.1002/adsc.202200272
• Cai, X.; Liu, Y.; Ding, S.; Fu, J.; Li, J.; Cheng, D.; Xu, X. Visible light-induced radical cascade reaction of acryloylbenzamides with N-hydroxyphthalimide esters. Tetrahedron Letters 2022, 95, 153722. doi:10.1016/j.tetlet.2022.153722
• Wang, X.; Liu, R.; Zhang, S.; Zhou, T.; Zhao, X.; Lu, K. Visible-light-induced radical cyclization of N-allylbenzamide with [Bis(difluoroacetoxy)iodo]benzene to difluoromethylated dihydroisoquinolinones. Tetrahedron Letters 2022, 96, 153761. doi:10.1016/j.tetlet.2022.153761
• Cheng, D.; Xu, X.; Fu, J.; Cai, X.; Liu, Y.; Li, J. Synthesis of Isoquinoline-1,3(2H,4H)-diones by Visible-Light-Mediated Cyclization of Acryloylbenzamides with Alkylboronic Acids, Arylsulfonyl Hydrazides and Oxime Esters. Synthesis 2022, 54, 2707–2723. doi:10.1055/a-1734-9782
• Yi, R.; Li, J.; Wang, D.; Wei, W. Radical Cascade Cyclization Involving C(sp3)—H Functionalization of Unactivated Cycloalkanes. Chinese Journal of Organic Chemistry 2022, 42, 4111. doi:10.6023/cjoc202208001
• Kulkarni, M. R.; Gaikwad, N. D. Recent Advances in Synthesis of 3,4-Dihydroisoquinolin-1(2H)-one. ChemistrySelect 2020, 5, 8157–8184. doi:10.1002/slct.202002131
• Su, Y.; Zhang, R.; Xue, W.; Liu, X.; Zhao, Y.; Wang, K.-H.; Huang, D.; Huo, C.; Hu, Y. Visible-light-promoted acyl radical cascade reaction for accessing acylated isoquinoline-1,3(2H,4H)-dione derivatives. Organic & biomolecular chemistry 2020, 18, 1940–1948. doi:10.1039/d0ob00086h
• Pan, C.; Wu, C.; Yuan, C.; Yu, J.-T. Cascade arylchloromethylation of unactivated alkenes for the construction of chloromethyl substituted dihydroisoquinolinones. Tetrahedron Letters 2020, 61, 151499. doi:10.1016/j.tetlet.2019.151499
• Li, Y.; Sun, S.; Cheng, J.; Yu, J.-T. Alkylarylation of N-allylbenzamides and N-allylanilines with simple ethers for the direct construction of ether substituted dihydroisoquinolinones and indolines. Organic & biomolecular chemistry 2020, 18, 650–654. doi:10.1039/c9ob02565k
• Pan, C.; Wang, Y.; Wu, C.; Yu, J.-T. Cascade arylalkylation of unactivated alkenes for the construction of cyanomethyl-substituted dihydroisoquinolinones and indolines. Catalysis Communications 2019, 131, 105802. doi:10.1016/j.catcom.2019.105802
• Liu, X.-C.; Sun, K.; Lv, Q.-Y.; Chen, X.; Sun, Y.; Peng, Y.; Qu, L.; Yu, B. Silver-mediated radical phosphorylation/cyclization of N-allylbenzamides to access phosphoryl-substituted dihydroisoquinolones. New Journal of Chemistry 2019, 43, 12221–12224. doi:10.1039/c9nj02833a
• Liu, X.-C.; Sun, K.; Chen, X.; Wang, W.; Liu, Y.; Li, Q.; Peng, Y.; Qu, L.; Yu, B. Visible-Light-Promoted Transition-Metal-Free Approach toward Phosphoryl-Substituted Dihydroisoquinolones via Cascade Phosphorylation/Cyclization of N-Allylbenzamides. Advanced Synthesis & Catalysis 2019, 361, 3712–3717. doi:10.1002/adsc.201900544

Explore citations to this article at