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 2022; 54(22): 5099-5109
DOI: 10.1055/a-1894-8303
DOI: 10.1055/a-1894-8303
paper
Visible-Light-Initiated Oxidative Coupling of Indole and Active Methylene Compounds Using Eosin Y as a Photocatalyst
Ambuj Kushwaha acknowledges the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for Senior Research Fellowship (SRF).
Abstract
A novel, efficient, mild, and inexpensive photocatalytic approach has been established for the visible-light-initiated oxidative coupling of indole and active methylene compounds using atmospheric air and water as an oxidant in the presence of Eosin Y to give 3-methyleneindolin-2-ones. In this work, only one molecule of malononitrile, ethyl acetoacetate, or dimedone reacts with one molecule of indole, but, in contrast, two molecules of barbituric acid react with one molecule of indole. The essential features of this approach are metal-free reaction, high yield of the products, no side product, and use of renewable energy sources.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1894-8303.
- Supporting Information
Publication History
Received: 03 March 2022
Accepted after revision: 08 July 2022
Accepted Manuscript online:
08 July 2022
Article published online:
08 August 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Wang H, Gao X, Lv Z, Abdelilah T, Lei A. Chem. Rev. 2019; 119: 6769
- 2 Morimoto K, Dohi T, Kita Y. Synlett 2017; 28: 1680
- 3 Mak JY, Pouwer RH, Williams CM. Angew. Chem. Int. Ed. 2014; 53: 13664
- 4 Mol J. Top. Catal. 2004; 27: 97
- 5 Sadrameli S. Fuel 2015; 140: 102
- 6 Bal TR, Anand B, Yogeeswari P, Sriram D. Bioorg. Med. Chem. Lett. 2005; 15: 4451
- 7 Jassim SA, Naji MA. J. Appl. Microbiol. 2003; 95: 412
- 8 Verma M, Pandeya SN, Singh KN, Stables JP. Acta Pharm. 2004; 54: 49
- 9 Tripathy R, Reiboldt A, Messina PA, Iqbal M, Singh J, Bacon ER, Angeles TS, Yang SX, Albom MS, Robinson C. Bioorg. Med. Chem. Lett. 2006; 16: 2158
- 10 de Oliveira Ferreira JM. G, da Silva GA, Coelho MC, Junior CG. L, Vale JA. Results Chem. 2021; 3: 100
- 11 Maury SK, Kumari S, Kushwaha AK, Kamal A, Singh HK, Kumar D, Singh S. Tetrahedron Lett. 2020; 61: 152
- 12 Maury SK, Kumar D, Kamal A, Singh HK, Kumari S, Singh S. Mol. Diversity 2021; 25: 131
- 13 Jiang X, Sun Y, Yao J, Cao Y, Kai M, He N, Zhang X, Wang Y, Wang R. Adv. Synth. Catal. 2012; 354: 917
- 14 Pogosyan S, Pogosyan M, Aleksanyan L, Safaryan A, Arakelyan A. Russ. J. Org. Chem. 2018; 54: 1860
- 15 Ghozlan SA. S, Ramadan MA, Abdelmoniem AM, Abdelhamid IA. Heterocycles 2016; 92: 1075
- 16 Ghozlan SA, Mohamed MF, Ahmed AG, Shouman SA, Attia YM, Abdelhamid IA. Arch. Pharm. 2015; 348: 113
- 17 Choi JH, Park CM. Adv. Synth. Catal. 2018; 360: 3553
- 18 Revathi L, Ravindar L, Fang WY, Rakesh K, Qin HL. Adv. Synth. Catal. 2018; 360: 4652
- 19 Zhu M, Fu W, Guo W, Tian Y, Wang Z, Ji B. Org. Biomol. Chem. 2019; 17: 3374
- 20 Yang H, Tian C, Qiu D, Tian H, An G, Li G. Org. Chem. Front. 2019; 6: 2365
- 21 Fu W, Han X, Zhu M, Xu C, Wang Z, Ji B, Hao X.-Q, Song M.-P. Chem. Commun. 2016; 52: 13413
- 22 Ghosh I, Ghosh T, Bardagi JI, König B. Science 2014; 346: 725
- 23 Romero NA, Margrey KA, Tay NE, Nicewicz DA. Science 2015; 349: 1326
- 24 Kamal A, Singh HK, Kumar D, Maury SK, Kumari S, Srivastava V, Singh S. ChemistrySelect 2021; 6: 52
- 25 Singh HK, Kamal A, Kumari S, Maury SK, Kushwaha AK, Srivastava V, Singh S. ChemistrySelect 2021; 6: 13982
- 26 Singh HK, Kamal A, Kumari S, Kumar D, Maury SK, Srivastava V, Singh S. ACS Omega 2020; 5: 29854
- 27 Yang X.-J, Chen B, Zheng L.-Q, Wu L.-Z, Tung C.-H. Green Chem. 2014; 16: 1082
- 28 Yang DT, Meng QY, Zhong JJ, Xiang M, Liu Q, Wu LZ. Eur. J. Org. Chem. 2013; 2013: 7528
- 29 Fidaly K, Ceballos C, Falguières A, Veitia MS.-I, Guy A, Ferroud C. Green Chem. 2012; 14: 1293
- 30 Teo YC, Pan Y, Tan CH. ChemCatChem 2013; 5: 235
- 31 Tan Z.-Y, Wu K.-X, Huang L.-S, Wu R.-S, Du Z.-Y, Xu D.-Z. Green Chem. 2020; 22: 332
- 32 Huang LS, Lai YH, Yang C, Xu DZ. Appl. Organomet. Chem. 2019; 33: e4910
- 33 Yue F, Dong J, Liu Y, Wang Q. Org. Lett. 2021; 23: 2477
- 34 Yue F, Dong J, Liu Y, Wang Q. Org. Lett. 2021; 23: 7306
- 35 Zhao Y, Zhang C, Chin KF, Pytela O, Wei G, Liu H, Bureš F, Jiang Z. RSC Adv. 2014; 4: 30062
- 36 Schilling W, Zhang Y, Riemer D, Das S. Chem. Eur. J. 2020; 26: 390
- 37 Kumari S, Kumar Maury S, Kumar Singh H, Kamal A, Kumar D, Singh S, Srivastava V. ChemistrySelect 2021; 6: 2980