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 2024; 56(16): 2529-2536
DOI: 10.1055/s-0043-1775369
DOI: 10.1055/s-0043-1775369
paper
Metal-Free Synthesis of Selanyl-Substituted Chromenones via Selanylation/Cyclization of Alkynyl Aryl Ketones
We would like to thank the National Natural Science Foundation of China (21861015), Guangxi Funds for Distinguished Experts, The Youth Promotion Fund of Guangxi (2024KY0527) and the Cultivation Plan of Thousands of Young and Middle-aged Backbone Teachers in Guangxi Colleges and Universities.
Abstract
A variety of 2-substituted 3-selanyl-chromenones are readily prepared through a cascade selanylation/cyclization of alkynyl aryl ketones with sulfonoselenoates. This transformation is performed under metal-free conditions and does not require an additional oxidant. It also has the advantage of broad functional group tolerance and scalability.
Key words
selanylation - 2-substituted 3-selanyl-chromenones - alkynyl aryl ketones - sulfonoselenoates - metal-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775369.
- Supporting Information
Publication History
Received: 26 March 2024
Accepted after revision: 21 May 2024
Article published online:
12 June 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Schlitzer SC, Arunprasath D, Stevens KG, Sharma I. Org. Chem. Front. 2020; 7: 913
- 1b Yang K, Li Q, Li Z, Sun X. Chem. Commun. 2023; 59: 5343
- 2a Zhang Q, Yuan P, Kai L, Liu K, Ban Y, Wang X, Wu L, Liu Q. Org. Lett. 2019; 21: 885
- 2b Khan I, Zaib S, Ibrar A. Org. Chem. Front. 2020; 7: 3734
- 2c Yang H, Duan X, Zhao J, Guo L. Org. Lett. 2015; 17: 1998
- 2d Matsumoto A, Lee H, Maruoka K. Chem. Rec. 2021; 21: 1342
- 3a Fan M, Yang W, He M, Li Y, Peng Z, Wang G. Eur. J. Med. Chem. 2022; 237: 114397
- 3b Bailly C. Bioorg. Med. Chem. 2021; 32: 116001
- 3c Roussel E, Moreno A, Altounian N, Philouze C, Peres B, Thomas A, Renaudet O, Falson P, Boumendjel A. Eur. J. Med. Chem. 2020; 202: 112503
- 4a Sun Y, Jiang P, Jiang Y, Pan J, Wu J, Li X, Guan W, Min X, Wang Y, Kuang H, Liu Y, Yang B. Bioorg. Chem. 2023; 134: 106447
- 4b Yu Z, Wang C, Zheng W, Chen D, Liu Y, Yang Y, Wei J. Bioorg. Chem. 2020; 99: 103789
- 5 Oliveira-Pinto S, Pontes O, Baltazar F, Costa M. Eur. J. Pharmacol. 2020; 887: 173452
- 6 Benny AT, Arikkatt SD, Vazhappilly CG, Kannadasan S, Thomas R, Leelabaiamma MS. N, Radhakrishnan EK, Shanmugam P. Mini-Rev. Med. Chem. 2022; 22: 1030
- 7a He X, Nie Y, Zhong M, Li S, Li X, Guo Y, Liu Z, Gao Y, Ding F, Wen D, Zhang Y. Eur. J. Med. Chem. 2021; 218: 113384
- 7b Chuai H, Zhang S, Bai H, Li J, Wang Y, Sun J, Wen E, Zhang J, Xin M. Eur. J. Med. Chem. 2021; 223: 113621
- 7c Sies H, Parnham MJ. Free Radical Biol. Med. 2020; 156: 107
- 7d Chen Z, Lai H, Hou L, Chen T. Chem. Commun. 2020; 56: 179
- 8a Hou W, Xu H. J. Med. Chem. 2022; 65: 4436
- 8b Wu Y, Chen J, Ning J, Jiang X, Deng J, Deng Y, Xu R, He W. Green Chem. 2021; 23: 3950
- 8c Li J, Liu X, Deng J, Huang Y, Pan Z, Yu Y, Cao H. Chem. Commun. 2020; 56: 735
- 9a Song Z, Ding C, Wang S, Dai Q, Sheng Y, Zheng Z, Liang G. Chem. Commun. 2020; 56: 1847
- 9b Sorabad GS, Maddani MR. New J. Chem. 2020; 44: 2222
- 9c Zhong S, Liu Y, Cao X, Wan J. ChemCatChem 2017; 9: 465
- 9d Ding C, Yu Y, Yu Q, Xie Z, Zhou Y, Zhou J, Liang G, Song Z. ChemCatChem 2018; 10: 5397
- 9e Yang Z, Hu L, Cao T, An L, Li L, Yang T, Zhou C. New J. Chem. 2019; 43: 16441
- 10 Godoi B, Sperança A, Bruning CA, Back DF, Menezes PH, Nogueira CW, Zeni G. Adv. Synth. Catal. 2011; 353: 2042
- 11 Du Y, Ai Z, Xiao J, Li Y, Guo B, Zhao K. Org. Chem. Front. 2020; 7: 3935
- 12 Lai J, Yin F, Guo Q, Yuan F, Nian B, Zhang M, Wu Z, Zhang H, Tang E. Org. Biomol. Chem. 2022; 20: 5104
- 13 Wang X, Meng J, Zhao D, Tang S, Sun K. Chin. Chem. Lett. 2023; 34: 107736
- 14a Sun S.-S, Mo Z.-Y, Chen Y.-Y, Xu Y.-L. J. Org. Chem. 2022; 87: 12447
- 14b Liu H, Zhang J, Huang G, Zhou Y, Chen Y, Xu Y. Adv. Synth. Catal. 2021; 363: 1656
- 14c Zhang J, Liu H, Fan T, Chen Y, Xu Y. Adv. Synth. Catal. 2021; 363: 497
- 14d Zhou X, Liu H, Mo Z, Ma X, Chen Y, Tang H, Pan Y, Xu Y. Chem Asian J. 2020; 15: 1536
- 14e Ma X, Wang Q, Feng X, Mo Z, Pan Y, Chen Y, Xin M, Xu Y. Green Chem. 2019; 21: 3547
- 14f Gong X, Sun S, Ren M, Wu Q, Chen Y, Xu Y. J. Org. Chem. 2024; 89: 4176
- 15 Anjos T, Gutterres EL, Barancelli DA, Cargnelutti R, Godoi B, Barcellos T, Schumacher RF. New J. Chem. 2023; 47: 1076
- 16a Zhang Z, Tan P, Wang S, Wang H, Xie L, Chen Y, Han L, Yang S, Sun K. Org. Lett. 2023; 25: 4208
- 16b Di Terlizzi L, Martinelli A, Merli D, Protti S, Fagnoni M. J. Org. Chem. 2023; 88: 6313
- 16c Zhang Q, Ban Y, Yuan P, Peng S, Fang J, Wu L, Liu Q. Green Chem. 2017; 19: 5559
- 17a Liu J, Wei W, Zhao T, Liu X, Wu J, Yu W, Chang J. J. Org. Chem. 2016; 81: 9326
- 17b Yang X, Li S, Liu H, Jiang Y, Fu H. RSC Adv. 2012; 2: 6549
- 17c Shi L, Zhang X, Zhang X. Tetrahedron 2016; 72: 8617
- 18 Bartz RH, Silva KB, Peglow TJ, Barcellos AM, Jacob RG, Lenardão EJ, Perin G. Org. Biomol. Chem. 2022; 20: 8952