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

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

Publikationsverlauf

Eingereicht: 02. November 2021

Angenommen nach Revision: 16. Dezember 2021

Artikel online veröffentlicht:
07. Februar 2022

• 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