RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2023; 55(21): 3693-3699
DOI: 10.1055/a-2124-5485
DOI: 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
A.K.B. acknowledges the SERB, DST (File no. EEQ/2018/000498) and University of Kalyani (PRG) for financial support. P.S. acknowledges Govt. of West Bengal for her SVMCM Fellowship. T.C. (URS) acknowledges the University of Kalyani for his fellowship. S.P. (CSIR-JRF) and S.D. (UGC-JRF) acknowledge the CSIR-New Delhi and UGC-New Delhi for their fellowships. The authors also acknowledge DST New Delhi for HRMS Facility at BITS Pilani, Pilani Campus under FIST scheme (SR/FST/CSI-270/2015).
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
photocatalyst-free - C–H selenylation - pyrazolo[1,5-a]pyrimidine - persulfate - visible lightSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2124-5485.
- Supporting Information
Publikationsverlauf
Eingereicht: 10. April 2023
Angenommen nach Revision: 06. Juli 2023
Accepted Manuscript online:
06. Juli 2023
Artikel online veröffentlicht:
21. August 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
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