Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

Salima Bouarfa; Ghenia Bentabed-Ababsa; William Erb; Laurent Picot; Valérie Thiéry; Thierry Roisnel; Vincent Dorcet; Florence Mongin

doi:10.1055/s-0040-1706542

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(07): 1271-1284
DOI: 10.1055/s-0040-1706542

paper

Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

Autoren

Salima Bouarfa

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

^bLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria eMail: bentabedg@gmail.com
Ghenia Bentabed-Ababsa∗

^bLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria eMail: bentabedg@gmail.com
William Erb

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France
Laurent Picot∗

^cLa Rochelle Université, Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, 17042 La Rochelle, France eMail: laurent.picot@univ-lr.fr
Valérie Thiéry

^cLa Rochelle Université, Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, 17042 La Rochelle, France eMail: laurent.picot@univ-lr.fr
Thierry Roisnel

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France
Vincent Dorcet

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France
Florence Mongin ∗

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

Abstract

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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

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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

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