Regioselective Suzuki–Miyaura Cross-Coupling Reactions of 2,6-Dichloroquinoxaline

Abstract

A variety of mono- and diarylated quinoxaline derivatives were prepared by site-selective Suzuki–Miyaura cross-coupling­ reactions of 2,6-dichloroquinoxaline. The selectivity is controlled by electronic parameters.

Key words

catalysis - palladium - Suzuki reaction - quinoxalines - regioselectivity

• References

• 1 Rajurkar RM, Agrawal VA, Thonte SS, Ingale RG. Pharmacophore 2010; 1: 65
• 2a Kumar S, Khan SA, Alam O, Azim R, Khurana A, Shaquiquzzaman M, Siddiqui N, Ahsan W. Bull. Korean Chem. Soc. 2011; 32: 2260
• 2b Umarani N, Ilango K. Int. J. Pharm. Sci. Rev. Res. 2010; 2: 24
• 2c Badran MM, Abouzid AM, Hussein MH. M. Arch. Pharmacal. Res. 2003; 26: 107
• 2d Kumar P, Kuamr A, Mohan LJ, Makrandi JK. Bull. Korean Chem. Soc. 2010; 31: 3304
• 2e Sridevi C, Balaji K, Naidu A, Sudhakaran R. E-J. Chem. 2009; 6: 866
• 2f Suresh M, Lavanya P, Sudhakar D, Vasu K, Rao CV. J. Chem. Pharm. Res. 2010; 2: 497
• 3a Sridevi C, Balaji K, Naidu A.  E-J. Chem. 2011; 8: 924
• 3b Burguete A, Pontiki E, Litina DH, Ancizu S, Villar R, Solano B, Moreno E, Torres E, Perez S, Aldana I, Monge A. Chem. Biol. Drug Des. 2011; 77: 255
• 4 Seitz LE, Suling WJ, Reynolds RC. J. Med. Chem. 2002; 45: 5604
• 5 Budakoti A, Bhat AR, Azam A. Eur. J. Med. Chem. 2009; 44: 1317
• 6 Chung HJ, Jung OJ, Chae MJ, Hong SY, Chung KH, Lee SK, Ryu CK. Bioorg. Med. Chem. Lett. 2005; 15: 3380
• 7 Kurasawa Y, Kim HS. J. Heterocycl. Chem. 1998; 35: 1101
• 8a Guillon J, Mouray E, Moreau S, Mullie C, Forfar I, Desplat V, Fabre SB, Pinaud N, Ravanello F, Le-Naour A, Leger JM, Gosmann G, Jarry C, Delaris G, Sonnet P, Grellier P. Eur. J. Med. Chem. 2011; 46: 2310
• 8b Barea C, Pabon A, Castillo D, Zimic M, Quiliano M, Galiano S, Silanes SP, Monge A, Deharo E, Aldana I. Bioorg. Med. Chem. Lett. 2011; 21: 4498
• 8c Guillon J, Forfar I, Desplat V, Fabre SB, Thiolat D, Massip S, Carrie H, Mossalayi D, Jarry C. J. Enzyme Inhib. Med. Chem. 2007; 22: 541

For reviews, see:
• 8d Hussain A, Madhesia D. J. Pharm. Res. 2011; 4: 924
• 8e Deepika Y, Nath PS, Sachin K, Shewta S. Int. J. Curr. Pharm. Rev. Res. 2011; 2: 33
• 9 Sheng R, Xu Y, Weng Q, Xia Q, He Q, Yang B, Hu Y. Drug Discovery Ther. 2007; 1: 119
• 10 Pradhan J, Sharma R, Goyal A. Int. J. Pharm. Res. Dev. 2010; 2 (06) Article No. 8
• 11 Servam P, Chandramohan M, Pannecouque C, De Clercq E. Int. J. Pharm. Ind. Res. 2011; 1: 2
• 12 Vicente E, Silanes SP, Lima LM, Ancizu S, Burguete A, Solano B, Villar R, Aldana I, Antonio M. Bioorg. Med. Chem. 2009; 17: 385
• 13 Gazit A, Yee K, Uecker A, Bohmer FD, Sjoblom T, Ostman A, Waltenberger J, Golomb G, Banai S, Heinrich MC, Levitzki A. Bioorg. Med. Chem. 2003; 11: 2007
• 14 You L, Cho EJ, Leavitt J, Ma LC, Montelione GT, Anslyn EV, Krug RM, Ellington A, Robertus JD. Bioorg. Med. Chem. Lett. 2011; 21: 3007
• 15a Waring M, Makoff A. Mol. Pharmacol. 1974; 10: 214
• 15b Kong D, Park EJ, Stephen AG, Galvani M, Cardellina JH, Monks A, Fisher RJ, Shoemaker RH, Melillo G. Cancer Res. 2005; 65: 9047
• 15c Wakelin LP. G. Med. Res. Rev. 1986; 6: 275
• 15d Lorenz KB, Diederichsen U. J. Org. Chem. 2004; 69: 3917
• 15e Bailly C, Waring MJ. Biochem. J. 1998; 330: 81
• 16 Baek JB, Harris FW. J. Polym. Sci., Part A: Polym. Chem. 2005; 43: 78
• 17a Dailey S, Feast WJ, Peace RJ, Sage IC, Till S, Wood EL. J. Mater. Chem. 2001; 11: 2238
• 17b Wang H, Chen G, Liu Y, Hu L, Xu X, Ji S. Dyes Pigm. 2009; 83: 269

• For reviews of site-selective palladium(0)-catalyzed cross-coupling reactions, see:

• 18a Schröter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245
• 18b Schnürch M, Flasik R, Khan AF, Spina M, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2006; 3283
• 18c Wang R, Manabe K. Synthesis 2009; 1405

• The Suzuki cross-coupling reaction of 2,6-dichloro-quinoxaline with one Boc-protected pyrazolylboronic acid pinacol ester has been reported in a patent. Surprisingly, the authors state the opposite regioselectivity for this reaction; see:

• 19a Boyle RG, Walker DW. WO 2010136755 (A1), 2010

For other palladium-catalyzed reactions of 2,6-dichloroquinoxaline (Sonogashira reaction), see:
• 19b Armengol M, Joule JA. J. Chem. Soc., Perkin Trans. 1 2001; 154
• 19c Armengol M, Joule JA. J. Chem. Soc., Perkin Trans. 1 2001; 978
• 20 CCDC 865782 (3g) and 865783 (5e) contain all crystallographic details for this publication. The data are available, free of charge, at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: [phone]; E-mail: [e-mail]]
• 21 Martin LJ, Marzinzik AL, Ley SV, Baxendale IR. Org. Lett. 2011; 13: 320