Silver-Catalyzed One-Pot Biarylamination of Quinones with Arylamines: Access to N-Arylamine-Functionalized p-Iminoquinone Derivatives

Yu Dong; Hui Jiang; Xiang-Long Chen; Ji-Xian Ye; Qiang Zhou; Long-Sen Gao; Qi-Qi Luo; Zhi-Chuan Shi; Zhong-Hui Li; Bing He

doi:10.1055/s-0041-1737340

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(09): 2242-2250
DOI: 10.1055/s-0041-1737340

paper

Silver-Catalyzed One-Pot Biarylamination of Quinones with Arylamines: Access to N-Arylamine-Functionalized p-Iminoquinone Derivatives

Authors

Yu Dong ∗

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Hui Jiang

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Xiang-Long Chen

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Ji-Xian Ye

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Qiang Zhou

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Long-Sen Gao

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Qi-Qi Luo

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Zhi-Chuan Shi

^bSouthwest Minzu University, Chengdu, 610041, P. R. China
Zhong-Hui Li∗

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China
Bing He∗

^aCollege of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. China

Abstract

Alle Artikel dieser Rubrik

Abstract

Concise one-pot biarylamination of quinones with arylamines was developed to synthesize N-arylamine-functionalized p-iminoquinones derivatives. The approach employed AgOAc as the catalyst and (NH₄)₂S₂O₈ as the oxidant in the presence of 3-chlorophenylboronic acid, giving a series of N-arylamine-functionalized p-iminoquinone derivatives in moderate to good yields whereas reaction in the absence of the 3-chlorophenylboronic acid, gave a series of N-arylamine-functionalized 1,4-naphthoquinone derivatives. This catalytic approach represents a step-economic and convenient strategy for the difunctionalization of quinones.

Key words

silver-catalyzed - biarylamination - quinones - arylamines - N-arylamine-functionalized p-iminoquinones

Volltext

Referenzen

References

1a Klare JE, Tulevski GS, Sugo K, De Picciotto A, White KA, Nuckolls C. J. Am. Chem. Soc. 2003; 125: 6030
1b Nowicka B, Kruk J. Biochim. Biophys. Acta. 2010; 1797: 1587
1c Petrangolini P, Alessandrini A, Facci P. J. Phys. Chem. C. 2013; 117: 17451

2a Adachi M, Murata Y, Nakamura S. J. Org. Chem. 1993; 58: 5238
2b Tao W, Barra M. J. Org. Chem. 2001; 66: 2158
2c Barra M, Tan A, Wong S. Dyes Pigm. 2004; 61: 63
2d Vittum PW, Brown GH. J. Am. Chem. Soc. 1946; 68: 2235
2e Josephy PD, Mason RP, Eling T. Carcinogenesis. 1982; 3: 1227

3a Imai S, Shimazu A, Furihata K, Furihata K, Hayakawa Y, Seto H. J. Antibiot. 1990; 43: 1606
3b Imai S, Noguchi T, Seto H. J. Antibiot. 1993; 46: 1232
3c Ren J, Liu D, Tian L, Wei Y, Proksch P, Zeng J, Lin W. Bioorg. Med. Chem. Lett. 2013; 23: 301
3d Gripenberg J. Acta Chem. Scand. 1958; 12: 603
3e Gomes PC. B, Nett M, Dahse H-M, Hertweck C. J. Nat. Prod. 2010; 73: 1461
3f Maskey R, Li F, Qin S, Fiebig H, Laatsch H, Chandrananimycins A. J. Antibiot. 2003; 56: 622

4 Bolognese A, Correale G, Manfra M, Lavecchia A, Mazzoni O, Novellino E, Barone V, Pani A, Tramontano E, La Colla P. J. Med. Chem. 2002; 45: 5205
5 Cortés-Salazar F, Beggah S, van der Meer JR, Girault HH. Biosens. Bioelectron. 2013; 47: 237

6a Albano E, Rundgren M, Harvison P, Nelson S, Moldeus P. Mol. Pharmacol. 1985; 28: 306
6b Stephanopoulos N, Carrico ZM, Francis MB. Angew. Chem. Int. Ed. 2009; 48: 9498
6c Chagas MP, Santos JC, Santos EB, Oliveira TD, Korn M. J. Braz. Chem. Soc. 2009; 20: 1646
6d Stephanopoulos N, Tong GJ, Hsiao SC, Francis MB. ACS Nano 2010; 4: 6014
6e Udit AK, Hackenberger CP, O’Reilly MK. ChemBioChem 2010; 11: 481

7a Bhattacharya S, Boone SR, Pierpont CG. J. Am. Chem. Soc. 1990; 112: 4561
7b Masui H, Lever A, Auburn PR. Inorg. Chem. 1991; 30: 2402
7c Bhattacharya S, Pierpont CG. Inorg. Chem. 1992; 31: 2020
7d Lever A, Masui H, Metcalfe R, Stufkens D, Dodsworth E, Auburn P. Coord. Chem. Rev. 1993; 125: 317
7e Whalen AM, Bhattacharya S, Pierpont CG. Inorg. Chem. 1994; 33: 347
7f Matson EM, Franke SM, Anderson NH, Cook TD, Fanwick PE, Bart SC. Organometallics 2014; 33: 1964

8a Siri O, Taquet J.-p, Collin JP, Rohmer MM, Bénard M, Braunstein P. Chem. Eur. J. 2005; 11: 7247
8b Taquet J.-p, Siri O, Braunstein P, Welter R. Inorg. Chem. 2006; 45: 4668
8c Yang Q.-Z, Kermagoret A, Agostinho M, Siri O, Braunstein P. Organometallics 2006; 25: 5518

9a Barret R, Daudon M. Tetrahedron Lett. 1991; 32: 2133
9b Coutts IG, Pavlidis VH, Reza K, Southcott MR, Wiley G. Tetrahedron Lett. 1997; 38: 5563
9c Myers AG, Tom NJ, Fraley ME, Cohen SB, Madar DJ. J. Am. Chem. Soc. 1997; 119: 6072
9d Nicolaou K, Baran P, Zhong Y.-L, Sugita K. J. Am. Chem. Soc. 2002; 124: 2212
9e Nicolaou K, Sugita K, Baran P, Zhong Y.-L. J. Am. Chem. Soc. 2002; 124: 2221
9f Quideau S, Pouységu L, Ozanne A, Gagnepain J. Molecules 2005; 10: 201
9g El Muslemany KM, Twite AA, ElSohly AM, Obermeyer AC, Mathies RA, Francis MB. J. Am. Chem. Soc. 2014; 136: 12600
9h Chandrasekar S, Sekar G. Org. Biomol. Chem. 2016; 14: 3053
9i Kühlborn J, Konhäuser M, Groß J, Wich PR, Opatz T. ACS Sustainable Chem. Eng. 2019; 7: 4414
9j Thysiadis S, Katsamakas S, Mpousis S, Avramidis N, Efthimiopoulos S, Sarli V. Bioorg. Chem. 2018; 80: 230

10 Ling T, Poupon E, Rueden EJ, Kim SH, Theodorakis EA. J. Am. Chem. Soc. 2002; 124: 12261
11 Zeng F.-L, Chen X.-L, He S.-Q, Sun K, Liu Y, Fu R, Qu L.-B, Zhao Y.-F, Yu B. Org. Chem. Front. 2019; 6: 1476
12 Yang J, Wang B, Zhang Y, Zhang S, He S, Shi Z.-C, Wang J.-Y. Org. Biomol. Chem. 2021; 19: 988

13a Zhang HB, Liu L, Chen YJ, Wang D, Li CJ. Adv. Synth. Catal. 2006; 348: 229
13b Lisboa C. dS, Santos VG, Vaz BG, de Lucas NC, Eberlin MN, Garden SJ. J. Org. Chem. 2011; 76: 5264
13c Dong Y, Ye J.-X, Luo Q.-Q, Mei T, Shen A, Huang P, Chen J, Zhang X, Xie C, Shi Z.-C. Synlett 2021; 32: 1772
13d Magar KB. S, Xia L, Lee YR. Chem. Commun. 2015; 51: 8592
13e Raju S, Annamalai P, Chen P.-L, Liu Y.-H, Chuang S.-C. Chem. Commun. 2017; 53: 6247

14 Sieveking I, Thomas P, Estévez JC, Quiñones N, Cuéllar MA, Villena J, Espinosa-Bustos C, Fierro A, Tapia RA, Maya JD, López-Muñoz R, Cassels BK, Estévez RJ, Salas CO. Bioorg. Med. Chem. 2014; 22: 4609
15 Huang L, Zhao J, Guo S, Zhang C, Ma J. J. Org. Chem. 2013; 78: 5627
16 Sharma U, Katoch D, Sood S, Kumar N, Singh B, Thakur A, Gulati A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2013; 52: 1431
17 Carceller R, García-Navío JL, Izquierdo ML, Alvarez-Builla J, Fajardo M, Gómez-Sal P, Gago F. Tetrahedron 1994; 50: 4995
18 Patil P, Nimonkar A, Akamanchi KG. J. Org. Chem. 2014; 79: 2331
19 Dong Y, Mei T, Luo Q.-Q, Feng Q, Chang B, Yang F, Zhou H.-w, Shi Z.-C, Wang J.-Y, He B. RSC Adv. 2021; 11: 6776
20 Wang S.-Y, Ji S.-J. Tetrahedron 2006; 62: 1527

Zusatzmaterial

Supporting Information (PDF)