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Synthesis 2021; 53(07): 1271-1284
DOI: 10.1055/s-0040-1706542
DOI: 10.1055/s-0040-1706542
paper
Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines
We thank the Université de Rennes 1 and the Centre National de la Recherche Scientifique (F.M.). We acknowledge the European Regional Development Fund (Fonds Européen de Développement Régional, FEDER; D8 VENTURE Bruker AXS diffractometer). L.P. and V.T. thank La Ligue contre le Cancer (French Cancer League; Comité 17 and Comité 86) for financial support and the Cancéropôle Grand Ouest (axis: Marine Molecules, Metabolism and Cancer 3MC) for scientific support. This research has been partly performed as part of the CNRS PICS project ‘Bimetallic synergy for the functionalization of heteroaromatics’.
Abstract
N-Arylation of various 2-acylated anilines with different electron-rich heteroaryl iodides (2- and 3-iodothiophenes, 2- and 3-iodobenzothiophenes, 2-iodobenzofuran) was achieved by using activated copper and potassium carbonate in dibutyl ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl or C3-free (benzo)furyl derivatives, affording original tri- and tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.
Key words
-
aniline -
thiophene -
iodine -
N-arylation -
copper -
antiproliferative activity -
melanoma cells
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706542.
- Supporting Information
- CIF File
Publication History
Received: 12 August 2020
Accepted after revision: 18 September 2020
Article published online:
26 October 2020
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References
- 1 Biehl ER. Top. Heterocycl. Chem. 2012; 29: 347
- 2 Rajappa S, Gumaste VK. Adv. Heterocycl. Chem. 2013; 108: 1
- 3a Bianchi L, Maccagno M, Petrillo G, Sancassan F, Tavani C, Morganti S, Rizzato E, Spinelli D. J. Org. Chem. 2007; 72: 5771
- 3b Kienle M, Wagner AJ, Dunst C, Knochel P. Chem. Asian J. 2011; 6: 517
- 3c Dunst C, Kienle M, Knochel P. Synthesis 2010; 2313
- 3d Martínez AM, Rodríguez N, Arrayás RG, Carretero JC. Chem. Commun. 2014; 50: 2801
- 3e Berzina B, Sokolovs I, Suna E. ACS Catal. 2015; 5: 7008
- 3f Shang M, Zeng S.-H, Sun S.-Z, Dai H.-X, Yu J.-Q. Org. Lett. 2013; 15: 5286
- 3g Yoon H, Lee Y. J. Org. Chem. 2015; 80: 10244
- 3h McDonald SL, Hendrick CE, Wang Q. Angew. Chem. Int. Ed. 2014; 53: 4667
- 3i McDonald SL, Hendrick CE, Bitting KJ, Wang Q. Org. Synth. 2015; 92: 356
- 3j Hendrick CE, Bitting KJ, Cho S, Wang Q. J. Am. Chem. Soc. 2017; 139: 11622
- 3k Bouarfa S, Grassl S, Ivanova M, Langlais T, Bentabed-Ababsa G, Lassagne F, Erb W, Roisnel T, Dorcet V, Knochel P, Mongin F. Eur. J. Org. Chem. 2019; 3244
- 4a Hornberger KR, Badiang JG, Salovich JM, Kuntz KW, Emmitte KA, Cheung M. Tetrahedron Lett. 2008; 49: 6348
- 4b Laing VE, Brookings DC, Carbery RJ, Simorte JG, Hutchings MC, Langham BJ, Lowe MA, Allen RA, Fetterman JR, Turner J, Meier C, Kennedy J, Merriman M. Bioorg. Med. Chem. Lett. 2012; 22: 472
- 5 Watanabe M, Yamamoto T, Nishiyama M. Chem. Commun. 2000; 133
- 6 Ogawa K, Radke KR, Rothstein SD, Rasmussen SC. J. Org. Chem. 2001; 66: 9067
- 7 Luker TJ, Beaton HG, Whiting M, Mete A, Cheshire DR. Tetrahedron Lett. 2000; 41: 7731
- 8 Begouin A, Hesse S, Queiroz M.-JR. P, Kirsch G. Synthesis 2005; 2373
- 9 Ferreira IC. F. R, Queiroz M.-JR. P, Kirsch G. Tetrahedron 2003; 59: 3737
- 10 Queiroz M.-JR. P, Begouin A, Ferreira IC. F. R, Kirsch G, Calhelha RC, Barbosa S, Estevinho LM. Eur. J. Org. Chem. 2004; 3679
- 11 Charles MD, Schultz P, Buchwald SL. Org. Lett. 2005; 7: 3965
- 12 Hooper MW, Utsunomiya M, Hartwig JF. J. Org. Chem. 2003; 68: 2861
- 13 Hooper MW, Hartwig JF. Organometallics 2003; 22: 3394
- 14 Elslager EF, Haley NF, McLean JR, Potoczak D, Veloso H, Wheelock RH. J. Med. Chem. 1972; 15: 61
- 15 Yang B, Mao Z, Zhu X, Wan Y. Catal. Commun. 2015; 60: 92
- 16 Lu Z, Twieg RJ. Tetrahedron 2005; 61: 903
- 17a Hedidi M, Bentabed-Ababsa G, Derdour A, Roisnel T, Dorcet V, Chevallier F, Picot L, Thiéry V, Mongin F. Bioorg. Med. Chem. 2014; 22: 3498
- 17b Ameur Messaoud MY, Bentabed-Ababsa G, Hedidi M, Derdour A, Chevallier F, Halauko YS, Ivashkevich OA, Matulis VE, Picot L, Thiéry V, Roisnel T, Dorcet V, Mongin F. Beilstein J. Org. Chem. 2015; 11: 1475
- 17c Hedidi M, Erb W, Bentabed-Ababsa G, Chevallier F, Picot L, Thiery V, Bach S, Ruchaud S, Roisnel T, Dorcet V, Mongin F. Tetrahedron 2016; 72: 6467
- 17d Amara R, Bentabed-Ababsa G, Hedidi M, Khoury J, Awad H, Nassar E, Roisnel T, Dorcet V, Chevallier F, Fajloun Z, Mongin F. Synthesis 2017; 49: 4500
- 17e Hedidi M, Maillard J, Erb W, Lassagne F, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T, Dorcet V, Hamzé M, Fajloun Z, Baratte B, Ruchaud S, Bach S, Bentabed-Ababsa G, Mongin F. Eur. J. Org. Chem. 2017; 5903
- 17f Lassagne F, Langlais T, Caytan E, Limanton E, Paquin L, Boullard M, Courtel C, Curbet I, Gédéon C, Lebreton J, Picot L, Thiéry V, Souab M, Baratte B, Ruchaud S, Bach S, Roisnel T, Mongin F. Molecules 2018; 23: 2961/1
- 17g Mokhtari Brikci-Nigassa N, Bentabed-Ababsa G, Erb W, Chevallier F, Picot L, Vitek L, Fleury A, Thiéry V, Souab M, Robert T, Ruchaud S, Bach S, Roisnel T, Mongin F. Tetrahedron 2018; 74: 1785
- 17h Mokhtari Brikci-Nigassa N, Nauton L, Moreau P, Mongin O, Duval RE, Picot L, Thiery V, Souab M, Baratte B, Ruchaud S, Bach S, Le Guevel R, Bentabed-Ababsa G, Erb W, Roisnel T, Dorcet V, Mongin F. Bioorg. Chem. 2020; 94: 103347
- 18 Nagaradja E, Chevallier F, Roisnel T, Dorcet V, Halauko YS, Ivashkevich OA, Matulis VE, Mongin F. Org. Biomol. Chem. 2014; 12: 1475
- 19 Murai M, Miki K, Ohe K. Chem. Commun. 2009; 3466
- 20a Rossi R, Bellina F, Lessi M. Adv. Synth. Catal. 2012; 354: 1181
- 20b Almond-Thynne J, Blakemore DC, Pryde DC, Spivey AC. Chem. Sci. 2017; 8: 40
- 21 Fairlamb IJ. S, O’Brien CT, Lin Z, Lam KC. Org. Biomol. Chem. 2006; 4: 1213
- 22 Robien W, Steindl H. Monatsh. Chem. 1985; 116: 685
- 23 Perry GJ. P, Quibell JM, Panigrahi A, Larrosa I. J. Am. Chem. Soc. 2017; 139: 11527
- 24 Belen’kii LI, Suslov IA, Chuvylkin ND. Chem. Heterocycl. Compd. 2003; 39: 36
- 25a Yu L.-Z, Hu X.-B, Xu Q, Shi M. Chem. Commun. 2016; 52: 2701
- 25b Wei P.-S, Wang M.-X, Xu D.-C, Xie J.-W. J. Org. Chem. 2016; 81: 1216
- 25c Sonawane AD, Garud DR, Udagawa T, Koketsu M. Org. Biomol. Chem. 2018; 16: 245
- 25d Li J, Tan E, Keller N, Chen Y.-H, Zehetmaier PM, Jakowetz AC, Bein T, Knochel P. J. Am. Chem. Soc. 2019; 141: 98
- 25e Teja C, Nawaz Khan FR. Org. Lett. 2020; 22: 1726
- 26a Nowacki M, Wojciechowski K. Synthesis 2017; 49: 3794
- 26b Khaikate O, Inthalaeng N, Meesin J, Kantarod K, Pohmakotr M, Reutrakul V, Soorukram D, Leowanawat P, Kuhakarn C. J. Org. Chem. 2019; 84: 15131
- 27a Kaida H, Goya T, Nishii Y, Hirano K, Satoh T, Miura M. Org. Lett. 2017; 19: 1236
- 27b Patil MD, Liu R.-S. Org. Biomol. Chem. 2019; 17: 4452
- 28 Yonekura K, Shinoda M, Yonekura Y, Tsuchimoto T. Molecules 2018; 23: 838
- 29a Salman GA, Hussain M, Iaroshenko V, Villinger A, Langer P. Adv. Synth. Catal. 2011; 353: 331
- 29b Gao W.-C, Liu T, Cheng Y.-F, Chang H.-H, Li X, Zhou R, Wei W.-L, Qiao Y. J. Org. Chem. 2017; 82: 13459
- 30a Rechfeld F, Gruber P, Kirchmair J, Boehler M, Hauser N, Hechenberger G, Garczarczyk D, Lapa GB, Preobrazhenskaya MN, Goekjian P, Langer T, Hofmann J. J. Med. Chem. 2014; 57: 3235
- 30b Ren H, Wang Y, Xing Y, Ran J, Liu M, Lei T, Zhou H, Li R, Sands JM, Yang B. Am. J. Physiol. 2014; 307: F1363
- 30c Gamboa de Dominguez ND, Charris J, Dominguez J, Monasterios M, Angel J, Rodrigues J. Exp. Parasitol. 2015; 155: 26
- 30d Leung E, Pilkington LI, van Rensburg M, Jeon CY, Song M, Arabshahi HJ, De Zoysa GH, Sarojini V, Denny WA, Reynisson J, Barker D. Bioorg. Med. Chem. 2016; 24: 1142
- 30e Abdelbaset MS, Abdel-Aziz M, Ramadan M, Abdelrahman MH, Abbas Bukhari SN, Ali TF. S, Abuo-Rahma GE.-D. A. Bioorg. Med. Chem. 2019; 27: 1076
- 31a Sichaem J, Rojpitikul T, Sawasdee P, Lugsanangarm K, Tip-Pyang S. Nat. Prod. Commun. 2015; 10: 1934578X1501000811
- 31b Perez M, Pis Diez CM, Belen Valdez M, Garcia M, Paola A, Avigliano E, Palermo JA, Blustein G. Chem. Biodiversity 2019; 16: e1900349
- 32 Bu X, Deady LW, Denny WA. Aust. J. Chem. 2000; 53: 143
- 33 Yang C.-L, Tseng C.-H, Chen Y.-L, Lu C.-M, Kao C.-L, Wu M.-H, Tzeng C.-C. Eur. J. Med. Chem. 2010; 45: 602
- 34 Liu B, Li F, Zhou T, Tang X.-Q, Hu G.-W. J. Heterocycl. Chem. 2018; 55: 1863
- 35a Deady LW, Kaye AJ, Finlay GJ, Baguley BC, Denny WA. J. Med. Chem. 1997; 40: 2040
- 35b Chen J, Deady LW, Desneves J, Kaye AJ, Finlay GJ, Baguley BC, Denny WA. Bioorg. Med. Chem. 2000; 8: 2461
- 36 Arzel E, Rocca P, Grellier P, Labaeïd M, Frappier F, Guéritte F, Gaspard C, Marsais F, Godard A, Queguiner G. J. Med. Chem. 2001; 44: 949
- 37 Bonjean K, De Pauw-Gillet MC, Defresne MP, Colson P, Houssier C, Dassonneville L, Bailly C, Greimers R, Wright C, Quetin-Leclercq J, Tits M, Angenot L. Biochemistry 1998; 37: 5136
- 38 Gottlieb HE, Kotlyar V, Nudelman A. J. Org. Chem. 1997; 62: 7512
- 39 Vogel AI, Tatchell AR, Furnis BS, Hannaford AJ, Smith PW. G. Vogel’s Textbook of Practical Organic Chemistry, 5th ed.. 1996
- 40 L’Helgoual’ch JM, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F. J. Org. Chem. 2008; 73: 177
- 41 Grubb AM, Schmidt MJ, Seed AJ, Sampson P. Synthesis 2012; 44: 1026
- 42 Tilly D, Snégaroff K, Dayaker G, Chevallier F, Gros PC, Mongin F. Tetrahedron 2012; 68: 8761
- 43 Hedidi M, Erb W, Lassagne F, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T, Bentabed-Ababsa G, Mongin F. RSC Adv. 2016; 6: 63185
- 44 Zhang C, De CK, Seidel D. Org. Synth. 2012; 89: 274
- 45 Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
- 46 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
- 47 Farrugia LJ. J. Appl. Crystallogr. 1997; 30: 565
- 48 Kawase Y, Yamaguchi S, Maeda O, Hayashi A, Hayashi I, Tabata K, Kondo M. J. Heterocycl. Chem. 1979; 16: 487
- 49 Lian Y, Hummel JR, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2013; 135: 12548
- 50 Klemm LH, McCoy DR, Klopfenstein CE. J. Heterocycl. Chem. 1971; 8: 383
- 51 Benati L, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G. J. Org. Chem. 2000; 65: 8669
- 52 Shanmugam P, Kanakarajan K, Soundararajan N. Z. Naturforsch., B 1976; 31: 1685
- 53 Gnanasekaran A, Soundararajan N, Shanmugam P. Synthesis 1977; 612
- 54 Ohhira Y, Kawase Y. J. Heterocycl. Chem. 1989; 26: 281