RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2025; 36(10): 1387-1390
DOI: 10.1055/a-2544-3496
DOI: 10.1055/a-2544-3496
letter
Synthesis of Benzo[c]isothiazole 2-Oxides via Copper-Catalyzed Cycloamidation Reaction
Authors
We are grateful for financial support from the National Natural Science Foundation of China (22361030), and the Natural Science Foundation of Guangxi Province (2022GXNSFAA035468, 2023GXNSFDA026063).
Abstract
Herein, a modular and efficient approach towards benzo[c]isothiazole 2-oxides via a copper-catalyzed intramolecular C–N cross-coupling reaction was disclosed. Readily available starting materials, broad substrate scope, outstanding yields (up to 95%), and scalability were observed, highlighting its potential in the pharmaceutical and chemical industries.
Key words
benzo[c]isothiazole 2-oxide - sulfoximine - C–N cross-coupling reaction - copper-catalyzed - Ullmann reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2544-3496.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 06. Februar 2025
Angenommen nach Revision: 21. Februar 2025
Accepted Manuscript online:
21. Februar 2025
Artikel online veröffentlicht:
15. Mai 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References and Notes
- 1a Dua R, Shrivastava S, Sonwane KS, Srivastava SK. Adv. Biol. Res. 2011; 5: 120
- 1b Baumann M, Baxendale RI. Beilstein J. Org. Chem. 2013; 9: 2265
- 1c Heterocyclic Chemistry in Drug Discovery. Li JJ. Wiley; Weinheim: 2013
- 1d Modern Crop Protection Compounds . Kraemer W, Schirmer U, Jeschke P, Witschel M. Wiley-VCH; Weinheim: 2012: 2
- 2a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
- 2b Lovering F. MedChemComm 2013; 4: 515
- 2c Bagdanoff JT, Xu Y, Dollinger G, Martin E. J. Med. Chem. 2015; 58: 5781
- 3a Rit RK, Yadav MR, Sahoo AK. Org. Lett. 2012; 14: 3724
- 3b Yadav MR, Rit RK, Sahoo AK. Chem. Eur. J. 2012; 18: 5541
- 3c Gosh K, Rit RK, Ramesh E, Sahoo AK. Angew. Chem. Int. Ed. 2016; 55: 7821
- 3d Le T.-N, Diter P, Pégot B, Bournaud C, Toffano M, Guillot R, Vo-Thanh G, Magnier E. Org. Lett. 2016; 18: 5102
- 4 Gais HJ. Heteroat. Chem. 2007; 18: 472
- 5a Okamura H, Bolm C. Chem. Lett. 2004; 33: 482
- 5b Frings M, Thmé I, Schiffers I, Pan F, Bolm C. Chem. Eur. J. 2014; 20: 1691
- 5c Benetskiy EB, Bolm C. Tetrahedron: Asymmetry 2011; 22: 373
- 5d Lemasson F, Gais H.-J, Runsink J, Raabe G. Eur. J. Org. Chem. 2010; 11: 2457
- 5e Frings M, Atodiresei I, Wang Y, Runsink J, Raabe G, Bolm C. Chem. Eur. J. 2010; 16: 5477
- 6a Harmata M, Rayanil K, Gomes MG, Zheng P, Calkins NL, Kim S.-Y, Fan Y, Bumbu V, Lee DR, Wacharasindhu S, Hong X. Org. Lett. 2005; 7: 143
- 6b Harmata M, Chen Y, Barnes CL. Org. Lett. 2007; 9: 5251
- 6c Pandey AG, McGrath MJ, Mancheño OG, Bolm C. Synthesis 2011; 3827
- 6d Dong W, Wang L, Parthasarathy K, Pan F, Bolm C. Angew. Chem. Int. Ed. 2013; 52: 11573
- 6e Yu D.-G, de Azambuja F, Glorius F. Angew. Chem. Int. Ed. 2014; 53: 2754
- 6f Cheng Y, Bolm C. Angew. Chem. Int. Ed. 2015; 54: 12349
- 6g Chinnagolla RK, Vijeta A, Jeganmohan M. Chem. Commun. 2015; 51: 12992
- 6h Jeon WH, Son JY, Kim JE, Lee PH. Org. Lett. 2016; 18: 3498
- 6i Cheng Y, Dong W, Wang H, Bolm C. Chem. Eur. J. 2016; 22: 10821
- 6j Cheng Y, Dong W, Parthasarathy K, Bolm C. Org. Lett. 2017; 19: 726
- 6k Huang J, Huang Y.-F, Wang T, Huang Q, Wang Z.-H, Chen Z.-Y. Org. Lett. 2017; 19: 1128
- 6l Wen J, Tiwari D.-P, Bolm C. Org. Lett. 2017; 19: 1706
- 6m Wen J, Cheng H, Raabe G, Bolm C. Org. Lett. 2017; 19: 6020
- 6n Ko GH, Son J.-Y, Kim H, Maeng C, Baek Y, Seo B, Um K, Lee P.-H. Adv. Synth. Catal. 2017; 359: 3362
- 6o Ma Y.-N, Guo C.-Y, Zhao Q, Zhang J, Chen X. Green Chem. 2018; 20: 2953
- 6p Zhou H, Chen W, Chen Z. Org. Lett. 2018; 20: 2590
- 6q Zheng G, Tian M, Xu Y, Chen X, Li X. Org. Chem. Front. 2018; 5: 998
- 6r Li L, Li Y, Zhao Z, Luo H, Ma Y.-N. Org. Lett. 2019; 21: 5995
- 6s Li S, Liu L, Wang R, Yang Y, Li J, Wei J. Org. Lett. 2020; 22: 7470
- 6t Ma Y.-N, Gao Y, Jing Y, Kang J, Zhang J, Chen X. J. Org. Chem. 2020; 85: 2918
- 6u Kong X, Lin L, Chen X, Chen Y, Wang W, Xu B. ChemSusChem 2021; 14: 3277
- 6v Zhou G, Zhou T, Jiang A.-L, Qian P.-F, Li J.-Y, Jiang B.-Y, Chen Z.-J, Shi B.-F. Angew. Chem. Int. Ed. 2024; 63: e202319871
- 6w Liu Z.-R, Herbert S, Schirok H, Ma C, Mei T.-S. Org. Lett. 2024; 26: 9034
- 6x Ren Y, Mo L, Wang Y, Yu L, Yin M, Xiong Z, Teng F, He Y. J. Org. Chem. 2024; 89: 3345
- 7a Ye W, Zhang L, Ni C, Rong J, Hu J. Chem. Commun. 2014; 50: 10596
- 7b Li Y, Dong L. Org. Biomol. Chem. 2017; 15: 9983
- 7c Yu H, Li Z, Bolm C. Angew. Chem. Int. Ed. 2018; 57: 12053
- 7d Lamers P, Bolm C. Org. Lett. 2018; 20: 116
- 7e Ma D, Kong DS, Wang CY, Truong K.-N, Rissanen K, Bolm C. Org. Lett. 2021; 23: 8287
- 7f Chang Y, Xie C, Liu H, Huang SL, Wang PF, Qin WL, Yan HL. Nat. Commun. 2022; 13: 1933
- 7g Wu P, Ward JS, Rissanen K, Bolm C. Adv. Synth. Catal. 2023; 365: 522
- 7h Liu LS, Liu YY, Li S, Gao J, Li J, Wei JF. J. Org. Chem. 2023; 88: 3626
- 7i Chakraborty N, Das B, Barik D, Rajbongshi KK, Patel BK. J. Org. Chem. 2024; 89: 778
- 8 Meanwell NA. J. Med. Chem. 2011; 54: 2529
- 9a Millemaggi A, Taylor RJ. K. Eur. J. Org. Chem. 2010; 4527
- 9b Ziarani GM, Gholamzadeh P, Lashgari N, Hajiabbasi P. ARKIVOC 2013; (i): 470
- 10a Claus PK, Hofbauer P, Rieder W. Tetrahedron Lett. 1974; 37: 3319
- 10b Lamers P, Buglioni L, Koschmieder S, Chatain N, Bolm C. Adv. Synth. Catal. 2016; 358: 3649
- 11 Tota A, Zenzola M, Chawner SJ, John-Campbell SS, Carlucci C, Romanazzi G, Degennaro L, Bull JA, Luisi R. Chem. Commun. 2017; 53: 348
- 12 Cycloamidation Reaction; General Procedure: A 15 mL Schlenk tube was charged with 1 (0.2 mmol), CuI (0.01 mmol, 5 mol%), and Cs2CO3 (0.2 mmol, 1.0 equiv) in 1,4-dioxane (1.0 mL) and the mixture was stirred at 60 °C in oil bath under Ar atmosphere for 4 h. Upon completion of the reaction (as determined by TLC analysis), EtOAc (10 mL) was added to the solution, the mixture was washed with brine, and the aqueous layer was washed with EtOAc (2 × 5 mL). The combined organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (EtOAc/hexane = 1:2) to afford target product 2.