Synthesis, Inhaltsverzeichnis Synthesis 2023; 55(21): 3693-3699DOI: 10.1055/a-2124-5485 special topic C–H Bond Functionalization of Heterocycles Photocatalyst-Free Visible-Light-Promoted C–H Selenylation of Pyrazolo[1,5-a]pyrimidines Papiya Sikdar a Department of Chemistry, University of Kalyani, Kalyani, W. B. 741235, India , Tathagata Choudhuri a Department of Chemistry, University of Kalyani, Kalyani, W. B. 741235, India , Suvam Paul a Department of Chemistry, University of Kalyani, Kalyani, W. B. 741235, India , Sourav Das a Department of Chemistry, University of Kalyani, Kalyani, W. B. 741235, India , Anil Kumar b Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani, Rajasthan 333031, India , Avik Kumar Bagdi ∗ a Department of Chemistry, University of Kalyani, Kalyani, W. B. 741235, India › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A new method has been developed for the C–H selenylation of pyrazolo[1,5-a]pyrimidine derivatives under the irradiation of visible light. This photocatalyst-free strategy is applicable to a wide range of pyrazolo[1,5-a]pyrimidines with broad functionalities. The salient features of the method are mild reaction conditions, use of bench-stable oxidant, high regioselectivity, and scalability. Key words Key wordsphotocatalyst-free - C–H selenylation - pyrazolo[1,5-a]pyrimidine - persulfate - visible light Volltext Referenzen References 1a Hassan AS, Morsy NM, Aboulthana WM, Ragab A. Drug Dev. Res. 2023; 84: 3 1b Cherukupalli S, Karpoormath R, Chandrasekaran B, Hampannavar GA, Thapliyal N, Palakollu VN. Eur. J. Med. Chem. 2017; 126: 298 1c Azeredo LF. S. P, Coutinho JP, Jabor VA. P, Feliciano PR, Nonato MC, Kaiser CR, Menezes CM. S, Hammes AS. O, Caffarena ER, Hoelz LV. B, de Souza NB, Pereira GA. N, Cerávolo IP, Krettli AU, Boechat N. Eur. J. Med. Chem. 2017; 126: 72 1d Hwang JY, Windisch MP, Jo S, Kim K, Kong S, Kim HC, Kim S, Kim H, Lee ME, Kim Y, Choi J, Park D.-S, Park E, Kwon J, Nam J, Ahn S, Cechetto J, Kim J, Liuzzi M, No Z, Lee J. Bioorg. Med. Chem. Lett. 2012; 22: 7297 2a Hammouda MM, Gafferc HE, Elattar KM. RSC Med. Chem. 2022; 13: 1150 2b Cherukupalli S, Hampannavar GA, Chinnam S, Chandrasekaran B, Sayyad N, Kayamba F, Aleti RR, Karpoormath R. Bioorg. Med. Chem. 2018; 26: 309 2c Zisapel N. Expert Opin. Invest. Drugs 2015; 24: 401 2d Chauhan M, Kumar R. Bioorg. Med. Chem. 2013; 21: 5657 3a Messaad M, Elleuch S, Kossentini M. J. Lumin. 2023; 257: 119772 3b Tigreros A, Portilla J. Eur. J. Org. Chem. 2022; e202200249 3c Tigreros A, Macías M, Portilla J. Dyes Pigm. 2021; 184: 108730 3d Tigreros A, Zapata-Rivera J, Portilla J. ACS Sustainable Chem. Eng. 2021; 9: 12058 3e Singsardar M, Sarkar R, Majhi K, Sinha S, Hajra A. ChemistrySelect 2018; 3: 1404 4a Arias-Gómez A, Godoy A, Portilla J. Molecules 2021; 26: 2708 4b Kumar H, Das R, Choithramani A, Gupta A, Khude D, Bothra G, Shard A. ChemistrySelect 2021; 6: 5807 4c Salem MA, Helal MH, Gouda MA, EL-Gawad HH. A, Shehab MA. M, El-Khalafawy A. Synth. Commun. 2019; 49: 1750 5a The Chemistry of Organic Selenium and Tellurium Compounds. Rappoport Z. Wiley; New York: 2013 5b Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium, 2nd ed. Devillanova FA, du Mont W.-W. RSC Publishing; Cambridge: 2013 5c Meena N, Kumar S, Shinde VN, Reddy SR, Himanshi, Bhuvanesh N, Kumar A, Joshi H. Chem Asian J. 2022; 17: e202101199 6a Sonam, Shinde VN, Rangan K, Kumar A. J. Org. Chem. 2023; 88: 2344 6b Azeredo JB, Penteado F, Nascimento V, Sancineto L, Braga AL, Lenardao EJ, Santi C. Molecules 2022; 27: 1597 6c Makhal PN, Nandi A, Kaki VR. ChemistrySelect 2021; 6: 663 6d Kibriya G, Samanta S, Singsardar M, Jana S, Hajra A. Eur. J. Org. Chem. 2017; 3055 6e Perin G, Nobre PC, Mailahn DH, Silva MS, Barcellos T, Jacob RG, Lenardão EJ, Santi C, Roehrs JA. Synthesis 2019; 51: 2293 6f Ivanova A, Arsenyan P. Coord. Chem. Rev. 2018; 370: 55 7a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596 7b Zhumagazy S, Zhu C, Yue H, Rueping M. Synlett 2023; 34: 1381 8a Bai R, Dabaria KK, Badsara SS. Synthesis 2022; 54: 2487 8b Zhang D, Zhang J, Li X, Yu Z, Li Y, Sun F, Du Y. Synthesis 2022; 54: 411 8c Schumacher RF, Cargnelutti R, Sperança A, Kazmierczak JC, Anjos T, Hartmann CM, Godoi B. Curr. Org. Chem. 2021; 25: 2068 8d Kundu D. RSC Adv. 2021; 11: 6682 8e Dey A, Hajra A. J. Org. Chem. 2019; 84: 14904 9 Protti S, Fagnoni M. ACS Org. Inorg. Au 2022; 2: 455 10a Ali D, Parvin T, Choudhury LH. J. Org. Chem. 2022; 87: 1230 10b Saba S, Rafique J, Franco MS, Schneider AR, Espíndola L, Silva DO, Braga AL. Org. Biomol. Chem. 2018; 16: 880 10c Zhang Q.-B, Ban Y.-L, Yuan P.-F, Peng S.-J, Fang J.-G, Wu L.-Z, Liu Q. Green Chem. 2017; 19: 5559 10d Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322 11a Zhu C, Zhumagazy S, Yue H, Rueping M. Chem. Commun. 2021; 58: 96 11b Lemir ID, Castro-Godoy WD, Heredia AA, Schmidt LC, Argüello JE. RSC Adv. 2019; 9: 22685 11c Yang D, Li G, Xing C, Cui W, Li K, Wei W. Org. Chem. Front. 2018; 5: 2974 11d Kumaraswamy G, Ramesh V, Gangadhar M, Vijaykumar S. Asian J. Org. Chem. 2018; 7: 1689 12a Tan X, Zhao K, Zhong X, Yang L, Dong Y, Wang T, Yu SLi X, Zhao Z. Org. Biomol. Chem. 2022; 20: 6566 12b Sahoo H, Mandal A, Dana S, Baidya M. Adv. Synth. Catal. 2018; 360: 1099 13a Saha S, Bagdi AK. Org. Biomol. Chem. 2022; 20: 3249 13b Mandal S, Bera T, Dubey G, Saha J, Laha JK. ACS Catal. 2018; 8: 5085 14a Das S, Paul S, Choudhuri T, Sikdar P, Bagdi AK. Synthesis 2023; 55: 2027 14b Bagdi AK, Rahman M, Bhattacherjee D, Zyryanov GV, Ghosh S, Chupakhin ON, Hajra A. Green Chem. 2020; 22: 6632 14c Bagdi AK, Hajra A. Org. Biomol. Chem. 2020; 18: 2611 Zusatzmaterial Zusatzmaterial Supporting Information
