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(12): 1958-1966
DOI: 10.1055/s-0042-1751570
DOI: 10.1055/s-0042-1751570
paper
Heptafluorobutyric Acid Catalyzed Cross-Dehydrogenative Coupling of 7-Aminocoumarins with 1,2,4-Triazines: A Straightforward Pathway to 3-Triazinyl-7-aminocoumarins
This work was supported by the Russian Science Foundation (grant no. 23-73-10050).
Abstract
A protocol for C–H/C–H cross-coupling reaction between 7-aminocoumarins and 1,2,4-triazines has been developed. The reaction was carried out under heptafluorobutyric acid catalysis providing products with yield up to 91%. The applicability and scope of the proposed method was demonstrated on 25 compounds containing different substituents both in the triazine ring and at the nitrogen atom of 7-aminocoumarins. The study of the reaction mechanism by EPR and radical trapping suggests that radicals are involved in this transformation.
Key words
7-aminocoumarin - cross-dehydrogenative coupling - 1,2,4-triazine - heptafluorobutyric acid - coumarin fluorophore - single electron transferSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751570.
- Supporting Information
Publication History
Received: 17 January 2024
Accepted after revision: 19 February 2024
Article published online:
01 March 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Udhayakumari D. Spectrochim. Acta, Part A. Mol. Biomol. Spectrosc. 2020; 228: 117817
- 2 Cao D, Liu Z, Verwilst P, Koo S, Jangjili P, Kim JS, Lin W. Chem. Rev. 2019; 119: 10403
- 3 Sun J, Zheng M, Jia J, Wang W, Cui Y, Gao J. Dyes Pigm. 2019; 164: 287
- 4 Smulik-Izydorczyk R, Dębowska K, Pięta J, Michalski R, Marcinek A, Sikora A. Free Radic. Biol. Med. 2018; 128: 69
- 5 Li X, Gao X, Shi W, Ma H. Chem. Rev. 2014; 114: 590
- 6 Liu Z, Helander MG, Wang Z, Lu Z. J. Phys. Chem. C 2010; 114: 11931
- 7 Sharma SJ, Sekar N. Dyes Pigm. 2022; 202: 110306
- 8 Erande Y, Sekar N. In Reviews in Fluorescence 2017. Geddes CD. Springer International Publishing; Cham: 2018: 123-144
- 9 Zhang L, Chen J, Zhang X, Wang Y, Cen J, Shi G, Sun M, Wang X, Meng W, Xiao K. Spectrochim. Acta, Part A. Mol. Biomol. Spectrosc. 2022; 275: 121171
- 10 Sun W.-X, Li N, Li Z.-Y, Yuan Y.-C, Miao J.-Y, Zhao B.-X, Lin Z.-M. Dyes Pigm. 2020; 182: 108658
- 11 Li Z, Yu C, Chen Y, Zhuang Z, Tian B, Liu C, Jia P, Zhu H, Yu Y, Zhang X, Sheng W, Zhu B. Dyes Pigm. 2020; 174: 108040
- 12 Reo YJ, Jun YW, Sarkar S, Dai M, Ahn KH. Anal. Chem. 2019; 91: 14101
- 13 Wang Y, Xu B, Sun R, Xu Y.-J, Ge J.-F. J. Mater. Chem. B 2020; 8: 7466
- 14 Goswami S, Das AK, Maity S. Dalton Trans. 2013; 42: 16259
- 15 Woll MG, Chen G, Choi S, Dakka A, Huang S, Karp GM, Lee C.-S, Li C, Narasimhan J, Naryshkin N, Paushkin S, Qi H, Turpoff AA, Weetall ML, Welch E, Yang T, Zhang N, Zhang X, Zhao X, Pinard E, Ratni H. WO Patent 2013101974, 2013
- 16 Nizamov S, Willig KI, Sednev MV, Belov VN, Hell SW. Chem. Eur. J. 2012; 18: 16339
- 17 Schill H, Nizamov S, Bottanelli F, Bierwagen J, Belov VN, Hell SW. Chem. Eur. J. 2013; 19: 16556
- 18 Nizamov S, Sednev MV, Bossi ML, Hebisch E, Frauendorf H, Lehnart SE, Belov VN, Hell SW. Chem. Eur. J. 2016; 22: 11631
- 19 Sarkar S, Shil A, Nandy M, Singha S, Reo YJ, Yang YJ, Ahn KH. Anal. Chem. 2022; 94: 1373
- 20 Rim Kim H, Sarkar S, Han Ahn K. Chem. Asian J. 2022; 17: e202101317
- 21 Krishnammagari SK, Balwe SG, Kim JS, Lim KT, Jeong YT. Monatsh. Chem. 2019; 150: 691
- 22 Chen Y, Wei X.-R, Sun R, Xu Y.-J, Ge J.-F. Org. Biomol. Chem. 2018; 16: 7619
- 23 Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
- 24 Khalymbadzha IA, Fatykhov RF, Chupakhin ON, Charushin VN, Tseitler TA, Sharapov AD, Inytina AK, Kartsev VG. Synthesis 2018; 50: 2423
- 25 Fatykhov RF, Khalymbadzha IA, Sharapov AD, Potapova AP, Starnovskaya ES, Kopchuk DS, Chupakhin ON. Chim. Techno Acta 2023; 10: 202310205
- 26 Fatykhov RF, Sharapov AD, Starnovskaya ES, Shtaitz YK, Savchuk MI, Kopchuk DS, Nikonov IL, Zyryanov GV, Khalymbadzha IA, Chupakhin ON. Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc. 2022; 267: 120499
- 27 Fatykhov RF, Savchuk MI, Starnovskaya ES, Bobkina MV, Kopchuk DS, Nosova EV, Zyryanov GV, Khalymbadzha IA, Chupakhin ON, Charushin VN, Kartsev VG. Mendeleev Commun. 2019; 29: 299
- 28 Khalymbadzha IA, Chupakhin ON, Fatykhov RF, Charushin VN, Schepochkin AV, Kartsev VG. Synlett 2016; 27: 2606
- 29 Fatykhov R, Khalymbadzha I, Chupakhin O. Adv. Synth. Catal. 2022; 364: 1052
- 30 Khalymbadzha IA, Fatykhov RF, Chupakhin ON. In Heterocycles via Cross Dehydrogenative Coupling: Synthesis and Functionalization. Srivastava A, Jana CK. Springer; Singapore: 2019: 35-75
- 31 Liu X, Cole JM, Waddell PG, Lin T.-C, Radia J, Zeidler A. J. Phys. Chem. A 2012; 116: 727
- 32 Fatykhov RF, Khalymbadzha IA, Sharapov AD, Potapova AP, Mochulskaya NN, Tsmokalyuk AN, Ivoilova AV, Mozharovskaia PN, Santra S, Chupakhin ON. Molecules 2022; 27: 7105
- 33 Utepova IA, Nemytov AI, Ishkhanian VA, Chupakhin ON, Charushin VN. Tetrahedron 2020; 76: 131391
- 34 Chupakhin ON, Shchepochkin AV, Charushin VN. Green Chem. 2017; 19: 2931
- 35 Utepova IA, Trestsova MA, Chupakhin ON, Charushin VN, Rempel AA. Green Chem. 2015; 17: 4401
- 36 Gustafson TP, Metzel GA, Kutateladze AG. Photochem. Photobiol. Sci. 2012; 11: 564
- 37 Chai J.-D, Head-Gordon M. J. Chem. Phys. 2008; 128: 084106
- 38 Najibi A, Goerigk L. J. Chem. Theory Comput. 2018; 14: 5725
- 39 Grimme S, Ehrlich S, Goerigk L. J. Comput. Chem. 2011; 32: 1456
- 40 Grimme S, Antony J, Ehrlich S, Krieg H. J. Chem. Phys. 2010; 132: 154104
- 41 Weigend F, Ahlrichs R. Phys. Chem. Chem. Phys. 2005; 7: 3297
- 42 Weigend F. Phys. Chem. Chem. Phys. 2006; 8: 1057
- 43 Adamo C, Barone V. J. Chem. Phys. 1999; 110: 6158
- 44 Stoll S, Schweiger A. J. Magn. Reson. 2006; 178: 42
- 45 Kutzelnigg W, Fleischer U, Schindler M. In Deuterium and Shift Calculation. NMR Basic Principles and Progress. Fleischer U, Kutzelnigg W, Limbach H.-H, Martin GJ, Martin ML, Schindler M. Springer; Berlin: 1991: 165-262
- 46 Pünkösti Z, Kele P, Herner A. J. Heterocycl. Chem. 2018; 55: 1183
- 47 Isaad J, El Achari A. J. Lumin. 2022; 243: 118668
- 48 Chen J, Liu W, Zhou B, Niu G, Zhang H, Wu J, Wang Y, Ju W, Wang P. J. Org. Chem. 2013; 78: 6121
- 49 Kamber DN, Liang Y, Blizzard RJ, Liu F, Mehl RA, Houk KN, Prescher JA. J. Am. Chem. Soc. 2015; 137: 8388
- 50 Courcot B, Tran DN, Fraisse B, Bonhomme F, Marsura A, Ghermani NE. Chem. Eur. J. 2007; 13: 3414
- 51 von Neunhoeffer H, Hennig H, Frühauf H.-W, Mutterer M. Tetrahedron Lett. 1969; 3147
- 52 Shintou T, Ikeuchi F, Kuwabara H, Umihara K, Itoh I. Chem. Lett. 2005; 34: 836