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-00000083.xml
Synlett
DOI: 10.1055/a-2616-5579
DOI: 10.1055/a-2616-5579
Letter
Deuterated Oxazoloisoindolinones via Photocatalytic Deoxygenative Cyclization of Amino Acid Derivatives
Supported by: National Natural Science Foundation of China 22371029

Abstract
A stereoselective synthesis of deuterated oxazoloisoindolinones using D2O was achieved through photocatalytic deoxygenation of readily available N-phthalimide amino acids, followed by an intramolecular 5-endo-trig cyclization. This protocol provides an efficient access to a broad array of deuterium-labeled N,O-heterobicycles with excellent deuterium incorporation.
Keywords
Amino acid - Photocatalytic deoxygenation - Cyclization - Deuterium incorporation - OxazoloisoindolinonePublication History
Received: 31 March 2025
Accepted after revision: 19 May 2025
Accepted Manuscript online:
20 May 2025
Article published online:
13 August 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Sulkowski TS. US Patent US 3336306A. 1967 15
- 1b Nagase T, Iino T, Sato Y, Nishimura T, Eiki J. Patent WO 2001014386. 2001
- 1c Oares J, Raimundo L, Pereira NAL. et al. Oncotarget 2016; 7: 4326
- 1d Soares J, Espadinha M, Raimundo L. et al. Mol Oncol 2017; 11: 612
- 1e Barcherini V, Almeida J, Lopes EA. et al. ChemMedChem 2021; 16: 250
- 2 Iino T, Sato Y, Nishimura T, Banba M, Eiki J, Nagase T. Patent JP2002255967. 2002 11.
- 3 Hatayama S, Hayashi K, Honma M, Takahashi I. Patent JP 2002220338. 2002
- 4a Cho CS, Chu DY, Lee DY. et al. Synth Commun 1997; 27: 4141
- 4b Ali MTM, Husin ZM, Macabeo APG. ACS Omega 2021; 6: 24614
- 5 Alladoum J, Vrancken E, Mangeney P, Roland S, Kadouri-Puchot C. Org Lett 2009; 11: 3746
- 6 Wu P, Nielsen TE. Chem Rev 2017; 117: 7811
- 7 Jing K, Wang X-N, Wang G-W. J Org Chem 2019; 84: 161
- 8 Takahashi H, Nagashima Y, Tanaka K. Eur J Org Chem. 1891 2021
- 9a Pinhoe Melo TMVD, Santos CIA. Tetrahedron Lett 2003; 44: 8285
- 9b Maity AK, Roy S. Adv Synth Catal 2014; 356: 2627
- 9c Wang Y, Zhao J, Qiao T, Zhang J, Chen G. Chin J Chem 2021; 39: 3297
- 10a Atzrodt J, Derdau V, Kerr WJ, Reid M. Angew Chem Int Ed 2018; 57: 1758
- 10b Di Martino RMC, Maxwell BD, Pirali T. Nat. Rev. Drug Discovery 2023; 22: 562
- 10c Chen J, Zhu Y-Y, Huang L, Zhang S-S, Gu S-X. Eur J Med Chem 2025; 287: 117371
- 11a Bergonzini G, Cassani C, Wallentin C-J. Angew Chem Int Ed 2015; 54: 14066
- 11b Ruzi R, Zhang M, Ablajan K, Zhu C. J Org Chem 2017; 82: 12834
- 11c Zhang M, Xie J, Zhu C. Nat Commun 2018; 9: 3517
- 11d Capaldo L, Riccardi R, Ravelli D, Fagnoni M. ACS Catal 2018; 8: 304
- 11e Bogonda G, Patil DV, Kim HY, Oh K. Org Lett 2019; 21: 3774
- 11f Li J, Liu Z, Wu S, Chen Y. Org Lett 2019; 21: 2077
- 11g Ding H, Xu K, Zeng C-C. J Catal 2020; 381: 38
- 11h Wang Z, Liu Q, Ji X, Deng G-J, Huang H. ACS Catal 2020; 10: 154
- 11i Zhu H-L, Zeng F-L, Chen X-L. et al. Org Lett 2021; 23: 2976
- 11j Zhu H-L, Zeng F-L, Chen X-L. et al. Org Lett 2021; 23: 2976
- 11k Bao L, Wang Z-X, Chen X-Y. Org Lett 2022; 24: 8223
- 11l Fan X, Sun X, Ji M. et al. Org Lett 2022; 24: 7271
- 11m Russo C, Donati G, Giustiniano F, Amato J, Marinelli L, Whitby RJ. Chem Eur J 2023; 29: e202301852
- 11n Shu H, Mo J-N, Liu W-D, Zhao J. Org Lett 2023; 25: 8677
- 11o Meng L, Yang C, Dong J, Wen W, Chen J, Fan B. Org Chem Front 2024; 11: 21
- 11p Tang W-H, Wu L-Y, Zhou Q-Q, Wan J-P. Org Chem Front 2025; 12: 2340
- 11q Ren J-W, Tan Q-L, Zuo J, Miao Y-F, Zhang P, Sun J-H. Org Chem Front 2025; 12: 577
- 12a Chatgilialoglu C, Crich D, Komatsu M, Ryu I. Chem Rev 1991; 1999: 99
- 12b Liu D, Liu C, Lei A. Chem Asian J 2015; 10: 2040
- 12c Zhou Y, Xu S, Zhang X, Zhou L, Zheng H, Zhu G. Chem Commun 2024; 60: 10098
- 13a Wang H, Xu W, Xin L, Liu W, Wang Z, Xu K. J Org Chem 2016; 81: 3681
- 13b Joshi A, Chandra Mohan D, Adimurthy S. Org Lett 2016; 18: 464
- 13c Cartwright KC, Tunge JA. ACS Catal 2018; 8: 11801
- 13d Krishna Rao MV, Reddy KN, Sridhar B, Subba Reddy BV. ChemistrySelect 2018; 3: 13110
- 13e Afanasenko A, Hannah R, Yan T, Elangovan S, Barta K. ChemSusChem 2019; 12: 3801
- 13f Cartwright KC, Lang SB, Tunge JA. J Org Chem 2019; 84: 2933
- 13g Shao X, Zheng Y, Tian L, Martín-Torres I, Echavarren AM, Wang Y. Org Lett 2019; 21: 9262
- 13h Merkens K, Aguilar Troyano FJ, Djossou J, Gómez-Suárez A. Adv Synth Catal 2020; 362: 2354
- 13i Pan S, Jiang M, Hu J, Xu R, Zeng X, Zhong G. Green Chem 2020; 22: 336
- 13j Zheng J, Nikbakht A, Breit B. ACS Catal 2021; 11: 3343
- 13k Manna S, Kakumachi S, Das KK, Tsuchiya Y, Adachi C, Panda S. Chem Sci 2022; 13: 9678
- 13l Zheng W-F, Chen J, Qi X, Huang Z. Nat Chem 2023; 15: 1672
- 13m Pitchai M, Ramirez A, Mayder DM. et al. ACS Catal 2023; 13: 647
- 13n Shi H, Wan Y, Zhang Y. Chin J Chem 2024; 42: 1341
- 13o Hu J, Liu L, Wang H, Huang L, Gao H, Feng H. Sustain Chem Pharm 2024; 38: 101441
- 13p Campbell ME, Ohler AR, McGill MJ, Buller AR. Angew Chem Int Ed 2025; e202422109
- 14a Kalutharage N, Yi CS. Angew Chem Int Ed 2013; 52: 13651
- 14b Klauck FJR, James MJ, Glorius F. Angew Chem Int Ed 2017; 56: 12336
- 14c Hoerrner ME, Baker KM, Basch CH, Bampo EM, Watson MP. Org Lett 2019; 21: 7356
- 14d Twitty JC, Hong Y, Garcia B. et al. J Am Chem Soc 2023; 145: 5684
- 14e Paul S, Brown MK. Angew Chem Int Ed 2024; 63: e202408432
- 15 Parajuli R, Arunan E. J Chem Sci 2015; 127: 1035
- 16a Stache EE, Ertel AB, Rovis T, Doyle AG. ACS Catal 2018; 8: 11134
- 16b Jiang H, Mao G, Wu H. et al. Green Chem 2019; 21: 5368
- 16c Ruzi R, Ma J, Yuan X-A. et al. Chem Eur J 2019; 25: 12724
- 16d Martinez Alvarado JI, Ertel AB, Stegner A, Stache EE, Doyle AG. Org Lett 2019; 21: 9940
- 16e Ruzi R, Liu K, Zhu C, Xie J. Nat Commun 2020; 11: 3312
- 16f Merkens K, Aguilar Troyano FJ, Anwar K, Gómez-Suárez A. J Org Chem 2021; 86: 8448
- 16g Ning Y, Wang S, Li M, Han J, Zhu C, Xie J. Nat Commun 2021; 12: 4637
- 16h Li Y, Shao Q, He H, Zhu C, Xue X-S, Xie J. Nat Commun 2022; 13: 10
- 16i Zhang L, Li Y, Guo Z. et al. Chin J Catal 2023; 50: 215
- 16j Su J, Chen A, Zhang G, Jiang Z, Zhao J. Org Lett 2023; 25: 8033
- 16k Wang H, Liu Z, Das A. et al. Nat Synth 2023; 2: 1116
- 16l Li Q, Chen J, Luo Y, Xia Y. Org Lett 2024; 26: 1517