Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis
DOI: 10.1055/a-2591-8986
DOI: 10.1055/a-2591-8986
paper
Synthesis of Benzofuro[3,2-c]isoquinolines through Anionic Intramolecular Cyclization
We thank the National Natural Science Foundation of China (22271268) for financial support.
Abstract
Benzofuro[3,2-c]isoquinolines are among the typical tetraheterocycles. The synthesis of benzofuro[3,2-c]isoquinoline derivatives in the presence of a catalytic amount of KOH has been developed. A variety of substituents could be tolerated. The base (KOH) works as a catalyst. A gram-scale synthesis was performed. Control experiments confirmed that a cascade anionic annulation is involved rather than a radical cyclization.
Key words
base - cascade annulation - tetraheterocycles - benzofuro[3,2-c]isoquinolines - transition-metal-free - catalyst freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2591-8986.
- Supporting Information
Publication History
Received: 16 March 2025
Accepted after revision: 21 April 2025
Accepted Manuscript online:
21 April 2025
Article published online:
08 May 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Marshall CM, Federice JG, Bell CN, Cox PB, Njardarson JT. J. Med. Chem. 2024; 67: 11622
- 2a Stępień M, Gońka E, Żyła M, Sprutta N. Chem. Rev. 2017; 117: 3479
- 2b Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 2020; 25: 1909
- 2c Martins P, Jesus J, Santos S, Raposo LR, Roma-Rodrigues C, Baptista PV, Fernandes AR. Molecules 2015; 20: 16852
- 2d Taylor AP, Robinson RP, Fobian YM, Blakemore DC, Jones LH, Fadeyi O. Org. Biomol. Chem. 2016; 14: 6611
- 2e Borissov A, Maurya YK, Moshniaha L, Wong W.-S, Żyła-Karwowska M, Stępień M. Chem. Rev. 2022; 122: 565
- 3a Kalugin VE, Shestopalov AM. Tetrahedron Lett. 2011; 52: 1557
- 3b Hsin L.-W, Chen C.-W, Chang L.-T. J. Chin. Chem. Soc. 2005; 52: 339
- 3c Cheng C.-Y, Hsin L.-W, Tsai M.-C, Schmidt WK, Smith C, Tam SW. J. Med. Chem. 1994; 37: 3121
- 3d Jagtap P, Roy A, Williams W. US Patent 7393955B2, 2008
- 3e Kim S, Park J, Joshi DR, Lee NK, Pham HL. B, Chung LK, Kang M, Kim Y, Kim I, Lee J. Dyes Pigm. 2022; 206: 110584
- 3f Chaban TI, Matiichuk YE, Horishny VY, Chaban IG, Matiychuk VS. Russ. J. Org. Chem. 2020; 56: 813
- 3g Pal S, Choudhary D, Jainth M, Kumar S, Tiwari RK, Verma AK. J. Org. Chem. 2016; 81: 9356
- 4 Béres M, Timári G, Hajós G. Tetrahedron Lett. 2002; 43: 6035
- 5 Zhu D, Wu Z, Luo B, Du Y, Liu P, Chen Y, Hu Y, Huang P, Wen S. Org. Lett. 2018; 20: 4815
- 6 Yu Z, Zhang Y, Tang J, Zhang L, Liu Q, Li Q, Gao G, You J. ACS Catal. 2020; 10: 203
- 7a Shan X.-H, Yang B, Zheng H.-X, Qu J.-P, Kang Y.-B. Org. Lett. 2018; 20: 7898
- 7b Shan X.-H, Yang B, Qu J.-P, Kang Y.-B. Chem. Commun. 2020; 56: 4063
- 7c Chen Y.-Z, Chen Y.-M, Hu Y, Qu J.-P, Kang Y.-B. Org. Lett. 2023; 25: 7518
- 7d Li Y.-W, Zheng H.-X, Yang B, Shan X.-H, Qu J.-P, Kang Y.-B. Org. Lett. 2020; 22: 4553
- 8 Zheng H.-X, Shan X.-H, Qu J.-P, Kang Y.-B. Org. Lett. 2018; 20: 3310
- 9 Shan X.-H, Zheng H.-X, Yang B, Tie L, Fu J.-L, Qu J.-P, Kang Y.-B. Nat. Commun. 2019; 10: 908
- 10 Yang Q, Li Y, Yang J.-D, Liu Y, Zhang L, Luo S, Cheng J.-P. Angew. Chem. Int. Ed. 2020; 59: 19282