Copper-Catalyzed Synthesis of 2-Arylbenzoxazoles in Tetrabutylammonium Bromide

Abstract

Copper-catalyzed synthesis of 2-arylbenzoxazoles from 1-bromo-2-iodobenzenes and benzamides in tetrabutylammonium bromide is described.

Key words

2-arylbenzoxazoles - heterocycles - copper - catalysis - tetrabutylammonium bromide

• References


For examples, see:
• 1a Huang S.-T, Hsei I.-J, Chen C. Bioorg. Med. Chem. 2006; 14: 6106
• 1b Oksuzoglu E, Tekiner-Gulbas B, Alper S, Temiz-Arpaci O, Ertan T, Yildiz I, Diril N, Sener-Aki E, Yalcin I. J. Enzyme Inhib. Med. Chem. 2008; 23: 37
• 1c Boyer J, Arnoult E, Médebielle M, Guillemont J, Unge J, Jochmans D. J. Med. Chem. 2011; 54: 7974
• 2a Yoshida S, Shiokawa S, Kawano K, Ito T, Murakami H, Suzuki H, Sato Y. J. Med. Chem. 2005; 48: 7075
• 2b Grobler JA, Dornadula G, Rice MR, Simcoe AL, Hazuda DJ, Miller MD. J. Biol. Chem. 2007; 282: 8005
• 2c Nishiu J, Ito M, Ishida Y, Kakutani M, Shibata T, Matsushita M, Shindo M. Diabetes Obes. Metab. 2006; 8: 508
• 2d Easmon J, Purstinger G, Thies K.-S, Heinisch G, Hofmann J. J. Med. Chem. 2006; 49: 6343
• 2e Rasmussen K, Hsu M.-A, Yang Y. Neuropsychopharmacology 2007; 32: 786
• 2f Leventhal L, Brandt MR, Cummons TA, Piesla MJ, Rogers KE, Harris HA. Eur. J. Pharmacol. 2006; 553: 146
• 2g Sessions EH, Yin Y, Bannister TD, Weiser A, Griffin E, Pocas J, Cameron MD, Ruiz C, Lin L, Schürer SC, Schröter T, LoGrasso P, Feng Y. Bioorg. Med. Chem. Lett. 2008; 18: 6390
• 3a Temiz O, Oren I, Sener E, Yalcin I, Ucarturk N. Farmaco 1998; 53: 337
• 3b Weidner-Vells MA, Ohemeng KA, Nguyen VN, Fraga-Spano S, Macielag MJ, Werblood HM, Foleno BD, Webb GC, Barrett JF, Hlasta DJ. Bioorg. Med. Chem. Lett. 2001; 11: 1545
• 3c Sacchi C, Magni F, Toia A, Cazzaniga F, Galli G, Berti F. Pharmacol. Res. 1989; 21: 177
• 3d Deorazio RJ, Nikam SS, Scott IL, Sherer BA. European Patent 1251128 A1 20021023, 2002 ; Chem. Abstr. 2002, 137, 310908.
• 3e Prucher H, Gottschlich R, Leibrock J. International Patent 9818793 A1 19980507, 1998 ; Chem. Abstr. 1998, 128, 321635.
• 3f Chancellor DR, Davies KE, Moor OD, Dorgan CR, Johnson PD, Lambert AG, Lawrence D, Lecci C, Maillol C, Middleton PJ, Nugent G, Poignant SD, Potter AC, Price PD, Pye RJ, Storer R, Tinsley JM, van Well R, Vickers R, Vile J, Wilkes FJ, Wilson FX, Wren SP, Wynne GM. J. Med. Chem. 2011; 54: 3241
• 3g Leaver IH, Milligan B. Dyes Pigm. 1984; 5: 109
• 4a Hein DW, Alheim RJ, Leavitt JJ. J. Am. Chem. Soc. 1957; 79: 427
• 4b Terashima M, Ishii M, Kanaoka Y. Synthesis 1982; 484
• 4c Bougrin K, Loupy A, Soufiaoui M. Tetrahedron 1998; 54: 8055
• 4d Pottorf RS, Chadha NK, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T, Player MR. Tetrahedron Lett. 2003; 44: 175
• 4e Kumar R, Selvam C, Kaur G, Chakraborti AK. Synlett 2005; 1401
• 5a Chang J, Zhao K, Pan S. Tetrahedron Lett. 2002; 43: 951
• 5b Varma RS, Saini RK, Prakash O. Tetrahedron Lett. 1997; 38: 2621
• 5c Park KH, Jun K, Shin SR, Oh SW. Tetrahedron Lett. 1996; 37: 8869
• 5d Srivastava RG, Venkataramani PS. Synth. Commun. 1988; 18: 1537
• 5e Varma RS, Kumar D. J. Heterocycl. Chem. 1998; 35: 1539
• 5f Praveen C, Kumar KH, Muralidharan D, Perumal PT. Tetrahedron 2008; 64: 2369
• 5g Kawashita Y, Nakamichi N, Kawabata H, Hayashi M. Org. Lett. 2003; 5: 3713
• 5h Kidwai M, Bansal V, Saxena A, Aerry S, Mozumdar S. Tetrahedron Lett. 2006; 47: 8049
• 5i Chen Y.-X, Qian L.-F, Zhang W, Han B. Angew. Chem. Int. Ed. 2008; 47: 9330
• 5j Blacker AJ, Farah MM, Hall MI, Marsden SP, Saidi O, Williams JM. J. Org. Lett. 2009; 11: 2039

For some examples, see:
• 6a Altenhoff G, Glorius F. Adv. Synth. Catal. 2004; 346: 1661
• 6b Viirre RD, Evinder G, Batey RA. J. Org. Chem. 2008; 73: 3452
• 6c Evindar G, Batey RA. J. Org. Chem. 2006; 71: 1802
• 6d Barbero N, Carril M, SanMartin R, Dominguez E. Tetrahedron 2007; 63: 10425
• 6e Tambade PJ, Patil YP, Qureshi ZS, Dhake KP, Bhanage BM. Synth. Commun. 2012; 42: 176
• 6f Bonnamour J, Bolm C. Org. Lett. 2008; 10: 2665
• 6g Ueda S, Nagasawa H. J. Org. Chem. 2009; 74: 4272

For examples, see:
• 7a Saha P, Ramana T, Purkait N, Ali MA, Paul R, Punniyamurthy T. J. Org. Chem. 2009; 74: 8719
• 7b Saha P, Ali MA, Punniyamurthy T. Org. Synth. 2011; 88: 398
• 7c Guru MM, Ali MA, Punniyamurthy T. Org. Lett. 2011; 13: 1194
• 7d Guru MM, Ali MA, Punniyamurthy T. J. Org. Chem. 2011; 76: 5295

For some examples, see:
• 8a Parvulescu VI, Hardacre C. Chem. Rev. 2007; 107: 2615
• 8b Dupont J, de Souza RF, Suarez PA. Z. Chem. Rev. 2002; 102: 3667
• 8c Welton T. Chem. Rev. 1999; 99: 2071
• 8d Martins MA. P, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG. Chem. Rev. 2008; 108: 2015
• 8e Greaves TL, Drummond CJ. Chem. Rev. 2008; 108: 206
• 8f Hallett JP, Welton T. Chem. Rev. 2011; 111: 3508

For some examples of using TBAB as a reaction medium, see:
• 9a Ali MA, Saha P, Punniyamurthy T. Synthesis 2010; 908
• 9b Tang B.-X, Wang F, Li J.-H, Xie Y.-X, Zhang M.-B. J. Org. Chem. 2007; 72: 6294
• 9c Calo V, Nacci A, Monopoli A, Laera S, Cioffi N. J. Org. Chem. 2003; 68: 2929
• 9d Li J.-H, Tang B.-X, Tao L.-M, Xie Y.-X, Liang Y, Zhang M.-B. J. Org. Chem. 2006; 71: 7488
• 9e Calo V, Nacci A, Monopoli A, Ferola V. J. Org. Chem. 2007; 72: 2596
• 10 Wang W, Zhan Y, Wang G. Chem. Commun. 2001; 727
• 11 Bönnemann H, Brijoux W In Active Metals: Preparation Characterization Applications. Fürstner A. Wiley-VCH; Weinheim: 1996: 339
• 12a Yang F, Wu Y, Zhu Z, Zhang J, Li Y. Tetrahedron 2008; 64: 6782
• 12b Marsden SP, McGonagle AE, McKeever-Abbas B. Org. Lett. 2008; 10: 2589
• 12c Peng J, Zong C, Ye M, Chen T, Gao D, Wang Y, Chen C. Org. Biomol. Chem. 2011; 9: 1225