Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines

Yitong Chen; Qi Zhu; Haiyang Wang; Yongping Yu; Wenteng Chen; Guolin Zhang

doi:10.1055/a-2051-0933

Synthesis, Table of Contents

Synthesis 2023; 55(16): 2554-2560
DOI: 10.1055/a-2051-0933

paper

Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines

Yitong Chen

,

Qi Zhu

,

Haiyang Wang

,

Yongping Yu

,

Wenteng Chen∗

,

Guolin Zhang∗

Abstract

All articles of this category

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 pyrazines

Full Text

References

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

Supplementary Material

Supporting Information