RSS-Feed abonnieren
DOI: 10.1055/a-2103-4915
Synthesis of 2-Benzyl-3-(2-oxo-2-phenylethyl)isoindolin-1-one Derivatives in Water under Catalyst-Free Conditions
This project was supported by the Natural Science Foundation of Jiangxi Province (Grant No. 20212ACB203001), the National Natural Science Foundation of China (Grant No. 21966003), and the Science and Technology Innovation Base Planning Project of Jiangxi (Grant No. 20202BCD42001).
Abstract
We have developed a catalyst-free synthesis of a series of isoindolinone derivatives via a one-pot, three-component reaction in water using o-formylbenzoic acids, primary amines, and acetophenones as starting materials. An investigation of the influence of the solvent, the substrate molar ratio, the temperature, and the reaction time revealed that the reaction proceeded optimally in water at 70 °C over 12 hours to afford a wide range of isoindolinone derivatives in yields of up to 93%. This method has the advantages of mild reaction conditions, environmental friendliness, and a broad substrate scope.
Key words
isoindolin-1-one - water - catalyst-free - three-component reaction - o-formylbenzoic acidSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2103-4915.
- Supporting Information
Publikationsverlauf
Eingereicht: 22. Dezember 2022
Angenommen nach Revision: 31. Mai 2023
Accepted Manuscript online:
31. Mai 2023
Artikel online veröffentlicht:
04. Juli 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Bao Y, Jiang S, Zhao L, Jin Y, Yan R, Wang Z. New J. Chem. 2020; 44: 19174
- 2 Krishna Y, Tanaka F. Org. Lett. 2021; 23: 1874
- 3 Miles DH, Yan X, Thomas-Tran R, Fournier J, Sharif EU, Drew SL, Jeffrey JL. ACS Med. Chem. Lett. 2020; 11: 2244
- 4 Yoshimoto R, Morisaka H, Usuki Y, Shibata Y, Tanaka K, Satoh T. Chem. Lett. 2020; 49: 1481
- 5 Jassem AM, Dhumad AM. Monatsh. Chem. 2020; 151: 1433
- 6 Savela R, Mendez-Galvez C. Chem. Eur. J. 2020; 27: 5344
- 7 Upadhyay SP, Thapa P, Sharma R, Sharma M. Fitoterapia 2020; 146: 104722
- 8 Wang L, Zhong J, Lin X. Synlett 2020; 32: 417
- 9 Cui W.-J, Wu Z.-J, Gu Q, You S.-L. J. Am. Chem. Soc. 2020; 142: 7379
- 10 Liu X.-Y, Luo X.-M, Tang L.-F. Tetrahedron 2020; 76: 131341
- 11 Pradhan S, Roy S, Banerjee S, De PB, Punniyamurthy T. J. Org. Chem. 2020; 85: 5741
- 12 Sadahiro Y, Kato H, Williams RM, Tsukamoto S. J. Nat. Prod. 2020; 83: 1368
- 13 Borja-Miranda A, Valencia-Villegas F, Lujan-Montelongo JA, Polindara-Garcia LA. J. Org. Chem. 2021; 86: 929
- 14 Jia X, Li P, Zhang X, Liu S, Shi X, Ma W, Dong H, Lu Y, Ni H, Zhao F. Eur. J. Org. Chem. 2020; 7343
- 15 Ryu I, Fukuyama T, Bando T. Synthesis 2018; 50: 3015
- 16 Dhanasekaran S, Suneja A, Bisai V, Singh VK. Org. Lett. 2016; 18: 634
- 17 Fukuyama T, Bando T, Ryu I. Synthesis 2018; 50: 3015
- 18 Karmakar R, Suneja A, Bisai V, Singh VK. Org. Lett. 2015; 17: 5650
- 19 Kundu SK, Kayet A, Baidya R, Satyanarayana L, Maiti DK. ACS Omega 2019; 5: 394
- 20 Solis-Santos M, Ordonez M, Ochoa-Teran A, Morales-Cueto R, Labastida-Galvan V. J. Photochem. Photobiol. A 2021; 413: 113185
- 21 Wang S.-M, Li C, Leng J, Bukhari SN. A, Qin HL. Org. Chem. Front. 2018; 5: 1411
- 22 Wu X, Wang B, Zhou S, Zhou Y, Liu H. ACS Catal. 2017; 7: 2494
- 23 Youn SW, Ko TY, Kim YH, Kim YA. Org. Lett. 2018; 20: 7869
- 24 Zhang Y, Zhu H, Huang Y, Hu Q, He Y, Wen Y, Zhu G. Org. Lett. 2019; 21: 1273
- 25 Chen F, Lei M, Hu L. Green Chem. 2014; 16, 2472
- 26 Han FZ, Su BB, Jia LN, Wang PW, Hu XP. Adv. Synth. Catal. 2017; 359: 146
- 27 Tian Y, Liu Q, Liu Y, Zhao R, Li G, Xu F. Tetrahedron Lett. 2018; 59: 1454
- 28 Le ZG, Lu Y, Jiang GF, Liu YS, Liu J, Xie ZB. J. Heterocycl. Chem. 2019; 56: 3135
- 29 Wang Z, Zhao B, Liu Y, Wan J.-P. Adv. Synth. Catal. 2022; 364: 1508
- 30 Palillero-Cisneros A, Bedolla-Medrano M, Ordóñez M. Tetrahedron 2018; 74: 4174
- 31 Zhang S, Shi X, Li J, Hou Z, Song Z, Su X, Zhao G. ACS Omega 2019; 4: 19420