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Synthesis 2014; 46(12): 1613-1620
DOI: 10.1055/s-0033-1341105
DOI: 10.1055/s-0033-1341105
paper
One-Pot Chemoselective Synthesis of 2,4,6,8-Tetrasubstituted Quinazolines via Microwave-Assisted Consecutive Bis-SNAr/Bis-Suzuki–Miyaura Cross-Coupling Reactions
Further Information
Publication History
Received: 14 January 2014
Accepted after revision: 13 March 2014
Publication Date:
02 April 2014 (online)
Abstract
A practical and efficient synthesis of 2,4,6,8-tetrasubstituted quinazolines through one-pot chemoselective sequential bis-SNAr/bis-Suzuki–Miyaura reactions under microwave irradiation is presented. The bis-SNAr reaction occurs selectively at the C-2 and C-4 positions of 6,8-dibromo-2,4-dichloroquinazoline and the bis-Suzuki–Miyaura cross-coupling at C-6 and C-8. This procedure affords convergent synthesis of polysubstituted quinazoline derivatives in high yields in very few steps and tolerates a wide range of boronic acids and amines.
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References
- 1a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 1b Suzuki A. Organomet. Chem. 1999; 576: 147
- 1c Kotha S, Lahiri K, Kashinath D. Tetrahedron 2002; 58: 9633
- 1d Bellina F, Carpita A, Rossi R. Synthesis 2004; 2419
- 1e Phan NT. S, Van Der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609
- 2 Kirchhoff JH, Netherton MR, Hills ID, Fu GC. J. Am. Chem. Soc. 2002; 124: 13662
- 3a Nicolaou KC, Montagnon T, Snyder SA. Chem. Commun. 2003; 551
- 3b Padwa A. Pure Appl. Chem. 2004; 76: 1933
- 3c Wu G, Yin W, Shen HC, Huang Y. Green Chem. 2012; 41: 580
- 3d Gembus V, Bonfanti J.-F, Querolle O, Jubault P, Levacher V, Hoarau C. Org. Lett. 2012; 14: 6012
- 4a Crozet MP, Archaimbault G, Vanelle P, Nouguier R. Tetrahedron Lett. 1985; 26: 5133
- 4b Roubaud C, Vanelle P, Maldonado J, Crozet MP. Tetrahedron 1995; 51: 9643
- 4c Amiri-Attou O, Terme T, Vanelle P. Molecules 2005; 10: 545
- 4d Castera-Ducros C, Paloque L, Verhaeghe P, Casanova M, Cantelli C, Hutter S, Tanguy F, Laget M, Remusat V, Cohen A, Crozet MD, Rathelot P, Azas N, Vanelle P. Bioorg. Med. Chem. 2013; 21: 7155
- 5a Kung P.-P, Casper MD, Cook KL, Wilson-Lingardo L, Risen LM, Vickers TA, Ranken R, Blyn LB, Wyatt JR, Dan Cook P, Ecker DJ. J. Med. Chem. 1999; 42: 4705
- 5b Jantova S, Spirkova K, Stankovsky S, Duchonova P. Folia Microbiol. 1999; 44: 187
- 5c Grovera G, Kini SG. Eur. J. Med. Chem. 2006; 41: 256
- 6a Chien T.-C, Chen C.-S, Yu F.-H, Chern J.-W. Chem. Pharm. Bull. 2004; 52: 1422
- 6b Herget T, Freitag M, Morbitzer M, Kupfer R, Stamminger T, Marschall M. Antimicrob. Agents Chemother. 2004; 48: 4154
- 7a Kunes J, Bazant J, Pour M, Waisser K, Slosarek M, Janota J. Farmaco 2000; 55: 725
- 7b Waisser K, Gregor J, Dostal H, Kunes J, Kubicova L, Klimesova V, Kaustova J. Farmaco 2001; 56: 803
- 8a Doyle LA, Ross DD. Oncogene 2003; 22: 7340
- 8b Henderson EA, Bavetsias V, Theti DS, Wilson SC, Clauss R, Jackman AL. Bioorg. Med. Chem. 2006; 14: 5020
- 9a Rewcastle GW, Palmer BD, Bridges AJ, Hollis Showalter HD, Sun L, Nelson J, McMichael A, Kraker AJ, Fry DW, Denny WA. J. Med. Chem. 1996; 39: 918
- 9b VanBrocklin HF, Lim JK, Coffing SL, Hom DL, Negash K, Ono MY, Gilmore JL, Bryant I, Riese II DJ. J. Med. Chem. 2005; 48: 7445
- 9c Cope H, Mutter R, Heal W, Pascoe C, Brown P, Pratt S, Chen B. Eur. J. Med. Chem. 2006; 41: 1124
- 9d Verhaeghe P, Azas N, Hutter S, Castera-Ducros C, Laget M, Dumètre A, Gasquet M, Reboul J.-P, Rault S, Rathelot P, Vanelle P. Bioorg. Med. Chem. 2009; 17: 4313
- 9e Kabri Y, Azas N, Dumètre A, Hutter S, Laget M, Verhaeghe P, Gellis A, Vanelle P. Eur. J. Med. Chem. 2010; 45: 616
- 10a Gautheron Chapoulaud V, Audoux J, Plé N, Turck A, Quéguiner G. Tetrahedron Lett. 1999; 40: 9005
- 10b Connolly DJ, Lacey PM, McCarthy M, Saunders CP, Carroll A.-M, Goddard R, Guiry PJ. J. Org. Chem. 2004; 69: 6572
- 10c Verhaeghe P, Azas N, Gasquet M, Hutter S, Ducros C, Laget M, Rault S, Rathelot P, Vanelle P. Bioorg. Med. Chem. Lett. 2008; 18: 396
- 10d Kabri Y, Gellis A, Vanelle P. Eur. J. Org. Chem. 2009; 4059
- 11a Mangalagiu I, Benneche T, Undheim K. Acta Chem. Scand. 1996; 50: 914
- 11b Mangalagiu I, Benneche T, Undheim K. Tetrahedron Lett. 1996; 37: 1309
- 11c Wipf P, George KM. Synlett 2010; 644
- 12a Kabri Y, Crozet MD, Szabo R, Vanelle P. Synthesis 2011; 3115
- 12b Kabri Y, Crozet MD, Primas N, Vanelle P. Eur. J. Org. Chem. 2012; 5595
- 13a Rahaim RJ. Jr, Maleczka RE. Jr. Tetrahedron Lett. 2002; 43: 8823
- 13b Cellier PP, Spindler J.-F, Taillefer M, Cristau H.-J. Tetrahedron Lett. 2003; 44: 7191
- 13c Handy ST, Bregman H, Lewis J, Zhang X, Zhang Y. Tetrahedron Lett. 2003; 44: 427
- 13d Navarro O, Marion N, Oonishi Y, Kelly III RA, Nolan SP. J. Org. Chem. 2006; 71: 685
- 13e Zawisza AM, Muzart J. Tetrahedron Lett. 2007; 48: 6738
- 13f Zeng M, Du Y, Shao L, Qi C, Zhang X.-M. J. Org. Chem. 2010; 75: 2556
- 14 Nakhai A, Stensland B, Svensson PH, Bergman J. Eur. J. Org. Chem. 2010; 6588
- 15 Zabeer A, Bhagat A, Gupta OP, Singh GD, Youssouf MS, Dhar KL, Suri OP, Suri KA, Satti NK, Gupta BD, Qazi GN. Eur. J. Med. Chem. 2006; 41: 429
- 16 Sheibley FE. J. Org. Chem. 1947; 12: 743
- 17 Volzhina ON, Azimov VA, Medvedev BA, Kazakov AA, Zhikhareva GP, Bondarenko VA, Yuzhakov SD, Dolgun OV, Mashkovskii MD, Yakhontov LN. Khim.-Farm. Zh. 1987; 21: 802 ; Chem. Abstr. 1987, 107, 211447