One-Pot Chemoselective Synthesis of 2,4,6,8-Tetrasubstituted Quinazolines via Microwave-Assisted Consecutive Bis-SNAr/Bis-Suzuki–Miyaura Cross-Coupling Reactions

Youssef Kabri; Maxime D. Crozet; Sébastien Redon; Patrice Vanelle

doi:10.1055/s-0033-1341105

Synthesis, Table of Contents

Synthesis 2014; 46(12): 1613-1620
DOI: 10.1055/s-0033-1341105

paper

One-Pot Chemoselective Synthesis of 2,4,6,8-Tetrasubstituted Quinazolines via Microwave-Assisted Consecutive Bis-S_NAr/Bis-Suzuki–Miyaura Cross-Coupling Reactions

Youssef Kabri

Aix-Marseille Université, Institut de Chimie Radicalaire ICR, UMR CNRS 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064, 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr

,

Maxime D. Crozet

Aix-Marseille Université, Institut de Chimie Radicalaire ICR, UMR CNRS 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064, 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr

,

Sébastien Redon

Aix-Marseille Université, Institut de Chimie Radicalaire ICR, UMR CNRS 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064, 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr

,

Patrice Vanelle*

Aix-Marseille Université, Institut de Chimie Radicalaire ICR, UMR CNRS 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064, 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr

› Author Affiliations

Abstract

All articles of this category

Abstract

A practical and efficient synthesis of 2,4,6,8-tetrasubstituted quinazolines through one-pot chemoselective sequential bis-S_NAr/bis-Suzuki–Miyaura reactions under microwave irradiation is presented. The bis-S_NAr 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.

Key words

quinazoline - Suzuki–Miyaura - chemoselectivity - microwave irradiation - palladium

Full Text

References

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