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 2023; 55(16): 2554-2560
DOI: 10.1055/a-2051-0933
DOI: 10.1055/a-2051-0933
paper
Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines
This research was supported by the Zhejiang Provincial Public Welfare Projects (Grant No. LGF22H300002).
Abstract
An efficient synthesis of unsymmetrical 2,6-disubstituted pyrazines was developed via a palladium(II)-catalyzed cascade reaction from aminoacetonitriles and arylboronic acids. This transformation involves a C(sp)–C(sp2) coupling followed by an intramolecular C–N bond formation in good to excellent yields.
Key words
C–C coupling - C–N bond formation - palladium catalysis - cascade reaction - 2,6-disubstituted pyrazinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2051-0933.
- Supporting Information
Publication History
Received: 01 December 2022
Accepted after revision: 09 March 2023
Accepted Manuscript online:
09 March 2023
Article published online:
19 April 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Kosuge T, Kamiya H. Nature 1962; 193: 776
- 2 Bohman B, Jeffares L, Flematti G, Byrne LT, Skelton BW, Phillips RD. J. Nat. Prod. 2012; 75: 1589
- 3 Cheng Z, Jiang S, Zhou Z. Biochem. Biophys. Res. Commun. 2021; 575: 8
- 4 Stancheva I, Georgiev G, Geneva M, Ivanova A, Dolezal M, Tumova L. J. Plant Nutr. 2010; 33: 818
- 5 Gong X, Xiang Y, Ning W, Zhan L, Gong S, Xie G, Yang C. J. Mater. Chem. C 2022; 10: 15981
- 6 Park H.-H, Meti P, Gong Y.-D. Dyes Pigm. 2021; 190: 109320
- 7 Brophy JJ, Cavill GW. K. Heterocycles 1980; 14: 477
- 8 Hassan NW, Saudi MN, Abdel-Ghany YS, Ismail A, Elzahhar PA, Sriram D, Nassra R, Abdel-Aziz MM, El-Hawash S. Bioorg. Chem. 2020; 96: 103610
- 9 Brown DG, Maier DL, Sylvester MA, Hoerter TN, Menhaji-Klotz E, Lasota CC, Hirata LT, Wilkins DE, Scott CW, Trivedi S, Chen T, McCarthy DJ, Maciag CM, Sutton EJ, Cumberledge J, Mathisen D, Roberts J, Gupta A, Liu F, Elmore CS, Alhambra C, Krumrine JR, Wang X, Ciaccio PJ, Wood MW, Campbell JB, Johansson MJ, Xia J, Wen X, Jiang J, Wang X, Peng Z, Hu T, Wang J. Bioorg. Med. Chem. Lett. 2011; 21: 3399
- 10 Nie S, Wu F, Wu J, Li X, Zhou C, Yao Y, Song Y. Eur. J. Med. Chem. 2022; 237: 114407
- 11 Gingipalli L, Block MH, Bao L, Cooke E, Dakin LA, Denz CR, Ferguson AD, Johannes JW, Larsen NA, Lyne PD, Pontz TW, Wang T, Wu X, Wu A, Zhang HJ, Zheng X, Dowling JE, Lamb ML. Bioorg. Med. Chem. Lett. 2018; 28: 1336
- 12 Niculescu-Duvaz I, Roman EL, Whittaker SR. J. Med. Chem. 2008; 51: 3261
- 13 Gorecki L, Muthna D, Merdita S, Andrs M, Kucera T, Havelek R, Muckova L, Kobrlova T, Soukup J, Krupa P, Prchal L, Soukup O, Roh J, Rezacova M, Korabecny J. Eur. J. Med. Chem. 2022; 240: 114580
- 14 Liu C, Zhao J, Qiao Y, Huang W, Rao Z. Tetrahedron 2018; 74: 7351
- 15 Prosenjit D, Yehoshoa B.-D, David M. J. Am. Chem. Soc. 2018; 140: 11931
- 16 Jia G, Lim Z, Zhang Y. Heteroat. Chem. 1998; 9: 341
- 17 Rizk T, Bilodeau EJ.-F, Beauchemin AM. Angew. Chem. Int. Ed. 2009; 48: 8325
- 18 Fernández M, Castaing M, Willis MC. Chem. Sci. 2017; 8,536
- 19 Veguillas M, Rojas-Martín J, Ribagorda M, Carreño MC. Org. Biomol. Chem. 2017; 15: 5386
- 20 Bunda S, Voronova K, Kathó Á, Udvardy A, Joó F. Molecules 2020; 25: 3993
- 21 Chen Y, He C, Chen J. Synth. Commun. 2022; 52: 1788
- 22 Luo H, Wang Z, Chen W, He C. Org. Prep. Proced. Int. 2021; 53: 127
- 23 Zhang G, Yu Y, Wang Z, Chen W, Luo H, He C. Synthesis 2020; 52: 1659
- 24 Wang Z, Chen W, He C. Tetrahedron 2020; 76: 130953
- 25 Teng W, Rajasekhar RN, Severin KT, Thomas RH. Nature 2016; 532: 484
- 26 Radl S, Hezký P, Urbankova J, Vachal P, Krejčí I. Collect. Czech. Chem. Commun. 2000; 65: 280
- 27 Marco JL, Ingate ST, Jaime C, Beá I. Tetrahedron 2000; 56: 2523
- 28 Yu J, Borzileiri RM, Villapati U. CN107406412A, 2016