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Synthesis 2025; 57(09): 1583-1591
DOI: 10.1055/a-2492-3240
DOI: 10.1055/a-2492-3240
feature
Synthesis of Isatins via Oxone®/TBAI-Mediated On-Water Oxidation of Indoles
Authors
This work was financially supported by the Council of Scientific and Industrial Research, India (CSIR, India) via Project Nos. HCP23 and HCP50. P.K. thanks CSIR for a fellowship. D.B. thanks CSIR-IIIM and CSIR-NCL for fellowships.

Abstract
Isatins and their derivatives are important scaffolds in a wide range of pharmaceuticals, bioactive compounds, and functional materials. Herein we describe a new strategy for the synthesis of isatins from indoles via Oxone®/TBAI-mediated oxidative dearomatization of indoles in water. The strategy works well with a variety of N-protected indoles and azaindoles.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2492-3240.
- Supporting Information (PDF)
Publication History
Received: 25 September 2024
Accepted after revision: 28 November 2024
Accepted Manuscript online:
28 November 2024
Article published online:
07 January 2025
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References
- 1a Varun, Sonam, Kakkar R. MedChemComm 2019; 10: 351
- 1b Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
- 2 Meena K, Kumari S, Khurana JM, Malik A, Sharma C, Panwar H. Chin. Chem. Lett. 2017; 28: 136
- 3 Guo H. Eur. J. Med. Chem. 2019; 164: 678
- 4a Teng O, Zhao H.-Y, Wang J, Liu JH, Gao HM.-L, Zhou Y, Han K.-L, Fan Z.-C, Zhang YM, Sun H, Yu P. Eur. J. Med. Chem. 2016; 112: 145
- 4b Ibrahim HS, Abou-Seri SM, Tanc M, Elaasser MM, Abdel-Aziz HA, Supuran CT. Eur. J. Med. Chem. 2015; 103: 583
- 5 Devale TL, Parikh J, Miniyar P, Sharma P, Shrivastava B, Murumkar P. Bioorg. Chem. 2017; 70: 256
- 6 Akhaja TN, Raval JP. Chin. Chem. Lett. 2012; 23: 785
- 7a Wanner MJ, Ingemann S, Maarseveen JH. V, Hiemstra H. Eur. J. Org. Chem. 2013; 1100
- 7b Mercedes A, Carlos R, Maria P, Elies M, Pedro F, Santos MM. M, Joan B. Chem. Commun. 2013; 49: 1954
- 7c Rasmussen HB, MacLeod JK. J. Nat. Prod. 1997; 60: 1152
- 7d Jnaneshwar GK, Deshpande VH. J. Chem. Res., Synop. 1999; 632
- 8a Sandmeyer T. Helv. Chim. Acta 1919; 2: 234
- 8b Chouhan M, Senwar KR, Sharma R, Grover V, Nair VA. Green Chem. 2011; 13: 2553
- 9a Stollé R. Ber. Dtsch. Chem. Ges. 1913; 46: 3915
- 9b Bryant WM, Huhn GF, Jensen JH, Pierce ME, Stammbach C. Synth. Commun. 1993; 23: 1617
- 10a Guyot A, Martinet J. C. R. Hebd. Seances Acad. Sci. 1913; 166: 1625
- 10b Hewawasam P, Meanwell NA. Tetrahedron Lett. 1994; 35: 7303
- 11 Yadav JS, Reddy BV. S, Reddy CS, Krishna AD. Synthesis 2007; 693
- 12 Kumar CN. S. S. P, Devi CL, Rao VJ, Palaniappan S. Synlett 2008; 2023
- 13a Zi Y, Cai Z.-J, Wang S.-Y, Ji S.-J. Org. Lett. 2014; 16: 3094
- 13b Bredenkamp A, Mohr F, Kirsch SF. Synthesis 2015; 47: 1937
- 13c Chandra A, Yadav NR, Moorthy JN. Tetrahedron 2019; 75: 2169
- 13d Liu P, Guo J, Wei W, Liu X, Sun P. Eur. J. Org. Chem. 2016; 2105
- 13e Rastogi GK, Deka B, Deb ML, Baruah PK. Asian J. Org. Chem. 2022; 11: e202100757
- 13f Wang CP, Jiang GF. Tetrahedron Lett. 2017; 58: 1747
- 14 Luo J, Zhao Y, Xu X, Zheng J, Liang H. Tetrahedron Lett. 2017; 58: 4591
- 15a Zhang C, Li S, Bureš F, Lee R, Ye X, Jiang Z. ACS Catal. 2016; 6: 6853
- 15b Schilling W, Zhang Y, Riemer D, Das S. Chem. Eur. J. 2020; 26: 390
- 16 Mainkar P, Ray A, Chandrasekhar S. ACS Omega 2024; 9: 7271
- 17a Hailes HC. Org. Process Res. Dev. 2007; 11: 114
- 17b Breslow R. The Principles of and Reasons for Using Water as a Solvent for Green Chemistry. In Handbook of Green Chemistry. Clark JH, Macquarrie DJ. Wiley-VCH; Weinheim: 2010
- 17c Hartonen K, Riekkola M.-L. Water as the First Choice Green Solvent . In The Application of Green Solvents in Separation Processes . Pena-Pereira F, Tobiszewski M. Elsevier; Amsterdam: 2017: 19-55
- 18 Kour J, Khajuria P, Sharma A, Sawant SD. Chem. Asian J. 2022; 17: e202200778
- 19 Li J, Cheng X, Ma X, Lv G, Zhan Z, Guan M, Wu Y. Synlett 2016; 27: 2485
- 20 Liu T, Yang H, Jiang Y, Fu H. Adv. Synth. Catal. 2013; 355: 1169
- 21 Zhang HH, Wang YQ, Huang LT, Zhu LQ, Feng YY, Lu YM, Zhao QY, Wang XQ, Wang Z. Chem. Commun. 2018; 54: 8265
- 22 Vijaykumar M, Pradhan C, Gonnade RG, Punji B. Org. Lett. 2023; 25: 1862
- 23 Tatsugi J, Zhiwei T, Izawa Y. ARKIVOC 2001; (i): 67
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