Late-Stage C–H Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one Backbone: Synthesis of an Array of Potential Kinase Inhibitors

Dedicated to the memory of Prof. Rolf Appel (25 February 1921 – 30 January 2012)
Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

Driven by the need of structural modification to establish structure-activity relationships, the regioselective C–H bond activation of thiazolo[5,4-f]quinazolin-9(8H)-one backbone has been developed to furnish the corresponding C2-arylated valuable scaffold. This strategy provides a synthetically streamlined and useful route for late-stage diversification of this attractive skeleton, required in drug discovery. A more eco-friendly synthesis of thiazolo[5,4-f]quinazolin-9(8H)-ones is also described giving access to these aforementioned compounds in a facile manner.

Key words

thiazoloquinazolinone - C–H arylation - palladium - microwave irradiation - Appel’s salt - kinase inhibition

• References

• 1 Wencel-Delord J. Glorius F. Nat. Chem. 2013; 5: 369
• 2a Rossi R. Lessi M. Manzini C. Marianetti G. Bellina F. Synthesis 2016; 48: 3821
• 2b Gayakhe V. Sanghvi YS. Fairlamb IJ. S. Kapdi AR. Chem. Commun. 2015; 51: 11944
• 2c Noisier AF. M. Brimble MA. Chem. Rev. 2014; 114: 8775
• 2d Hong J. Chem. Eur. J. 2014; 20: 10204
• 2e Rossi R. Bellina F. Lessi M. Manzini C. Perego LA. Synthesis 2014; 46: 2833
• 2f Chen DY.-K. Youn SW. Chem. Eur. J. 2012; 18: 9452
• 2g Yamaguchi J. Yamaguchi AD. Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
• 2h Godula K. Sames D. Science 2006; 312: 67
• 3 Hédou D. Dubouilh-Benard C. Loaëc N. Meijer L. Fruit C. Besson T. Molecules 2016; 21: 794

For recent papers relating the biological interest of 9-aminothiazolo[5,4-f]quinazoline derivatives, see:
• 4a Chaikuad A. Diharce J. Schröder M. Foucourt A. Leblond B. Casagrande A.-S. Désire L. Bonnet P. Knapp S. Besson T. J. Med. Chem. 2016; 59: 10315
• 4b Courtadeur S. Benyamine H. Delalonde L. de Oliveira C. Leblond B. Foucourt A. Besson T. Casagrande A.-S. Taverne T. Girard A. Pando MP. Désiré L. J. Neurochem. 2015; 133: 440
• 4c Abbassi R. Johns TG. Kassiou M. Munoz L. Pharmacol. Ther. 2015; 151: 87
• 4d Deng X. Hu J. Ewton DZ. Friedman E. Carcinogenesis 2014; 35: 1968
• 4e Deng X. Mercer SE. Sun CY. Friedman E. Genes Cancer 2014; 5: 337
• 4f Deng X. Hu J. Cunningham MJ. Friedman E. Genes Cancer 2014; 5: 201
• 4g Deng X. Mercer SE. Sun CY. Friedman E. Genes Cancer 2014; 5: 22
• 4h Leblond B. Casagrande A.-S. Désiré L. Foucourt A. Besson T. Patent WO 2013026806, 2013 ; Chem. Abst. 2013, 158, 390018
• 5a Harari M. Couly F. Fruit C. Besson T. Org. Lett. 2016; 18: 3282
• 5b Fruit C., Harari M., Couly F., Besson T.; In Proceedings of the 20th Int. Electron. Conf. Synth. Org. Chem., 1–30 November 2016, Sciforum Electronic Conference Series Vol. 20; 2016, b002; doi: 10.3390/ecsoc-20-b002
• 6a Rosini M. Simoni E. Caporaso R. Minarini A. Future Med. Chem. 2016; 8: 697
• 6b Guzior N. Wieckowska A. Panek D. Malawska B. Curr. Med. Chem. 2015; 22: 373
• 6c Katselou MG. Matralis AN. Kourounakis AP. Curr. Med. Chem. 2014; 21: 2743
• 6d Leon R. Garcia AG. Marco-Contelles J. Med. Res. Rev. 2013; 33: 139
• 6e León R. Marco-Contelles J. Curr. Med. Chem. 2011; 18: 552
• 6f Cavalli A. Bolognesi ML. Minarini A. Rosini M. Tumiatti V. Recanatini M. Melchiorre C. J. Med. Chem. 2008; 51: 347
• 7a Hédou D. Guillon R. Lecointe C. Logé C. Chosson E. Besson T. Tetrahedron 2013; 69: 3182
• 7b Testard A. Picot L. Lozach O. Blairvac M. Meijer L. Murillo L. Piot J.-M. Thiéry V. Besson T. J. Enz. Inhib. Med. Chem. 2005; 20: 557
• 7c Alexandre F.-R. Berecibar A. Wrigglesworth R. Besson T. Tetrahedron Lett. 2003; 44: 4455
• 8a Leadbeater NE. In Comprehensive Organic Synthesis . Knochel P. Molander GA. Elsevier; Oxford: 2014. 2nd ed., Vol. 9 234
• 8b Bazureau JP. Paquin L. Carrie D. L’Helgoual’ch J.-M. Guiheneuf S. Coulibaly K.-W. Burgy G. Komaty S. Limanton E. In Microwaves in Organic Synthesis . de la Hoz A. Loupy A. Wiley-VCH; Weinheim: 2012
• 8c Sharma A. Appukkuttan P. Van der Eycken E. Chem. Commun. 2012; 48: 1623
• 8d Dallinger D. Kappe CO. Chem. Rev. 2007; 107: 2563
• 8e Microwave Methods in Organic Synthesis . Larhed M. Olofsson K. Springer; Berlin: 2006
• 8f Microwave-Assisted Organic Synthesis . Lidström P. Tierney JP. Blackwell; Oxford: 2005
• 8g Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
• 9 Unpublished results.
• 10a Barba F. Recio J. Batanero B. Tetrahedron Lett. 2013; 54: 1835
• 10b Ding S. Jiao N. Angew. Chem. Int. Ed. 2012; 51: 9226
• 10c Loidreau Y. Besson T. Tetrahedron 2011; 67: 4852
• 10d Muzart J. Tetrahedron 2009; 65: 8313
• 10e Nouira I. Kostakis IK. Dubouilh C. Chosson E. Iannelli M. Besson T. Tetrahedron Lett. 2008; 49: 7033
• 10f Kostakis IK. Elomri A. Seguin E. Iannelli M. Besson T. Tetrahedron Lett. 2007; 48: 6609
• 10g Agarwal A. Chauhan PM. S. Synth. Commun. 2004; 34: 2925
• 11a Chen X. Yang Q. Zhou Y. Deng Z. Mao X. Peng Y. Synthesis 2015; 47: 2055
• 11b Cechov L. Jansa P. Sala M. Dracínsky M. Holy A. Janeba Z. Tetrahedron 2011; 67: 866
• 12a Garcia J. Sorrentino J. Diller EJ. Chapman D. Woydziak ZR. Synth. Commun. 2016; 46: 475
• 12b Bolchi C. Pallavicini M. Binda M. Fumagalli L. Valoti E. Tetrahedron: Asymmetry 2012; 23: 217
• 12c Sharma A. Mehta VP. Van der Eycken E. Tetrahedron 2008; 64: 2605
• 12d Cho YH. Park JC. Tetrahedron Lett. 1997; 38: 8331
• 13 Liu W. Chen C. Liu H. Beilstein J. Org. Chem. 2015; 11: 1721
• 14a Petersen TP. Larsen AF. Ritzén A. Ulven T. J. Org. Chem. 2013; 78: 4190
• 14b Larsen AF. Ulven T. Org. Lett. 2011; 13: 3546
• 15a Laclef S. Harari M. Godeau J. Schmitz-Afonso I. Bischoff L. Hoarau C. Levacher V. Fruit C. Besson T. Org. Lett. 2015; 17: 1700
• 15b Godeau J. Harari M. Laclef S. Deau E. Fruit C. Besson T. Eur. J. Org. Chem. 2015; 7705
• 15c Fruit C. Godeau J. Harari M. Laclef S. Levacher V. Besson T. In Proceedings of the 1st Int. Electron. Conf. Med. Chem., 2–27 November 2015, ­Sciforum Electronic Conference Series Vol. 1. A004. 2015.
• 16a Rossi R. Lessi M. Manzini C. Marianetti G. Bellina F. Tetrahedron 2016; 72: 1795
• 16b Bheeter CB. Chen L. Soulé J.-F. Doucet H. Catal. Sci. Technol. 2016; 6: 2005
• 16c Théveau L. Schneider C. Fruit C. Hoarau C. ChemCatChem 2016; 8: 3183
• 16d El Kazzouli S. Koubachi J. El Brahmi N. Guillaumet G. RSC Adv. 2015; 5: 15292
• 16e Segawa Y. Maekawa T. Itami K. Angew. Chem. Int. Ed. 2015; 54: 66
• 16f Rossi R. Bellina F. Lessi M. Manzini C. Adv. Synth. Catal. 2014; 356: 17
• 16g Kapdi AR. Dalton Trans. 2014; 43: 3021
• 16h Bonin H. Sauthier M. Felpin F.-X. Adv. Synth. Catal. 2014; 356: 645
• 16i Shibahara F. Murai T. Asian J. Org. Chem. 2013; 2: 624
• 16j Ackermann L. Chem. Rev. 2011; 111: 1315
• 16k Hirano K. Miura M. Synlett 2011; 294
• 16l Daugulis O. Top. Curr. Chem. 2010; 292: 57
• 16m Bellina F. Rossi R. Tetrahedron 2009; 65: 10269
• 16n Seregin IV. Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
• 16o Fairlamb IJ. S. Chem. Soc. Rev. 2007; 36: 1036

For reviews on C–H arylation under microwave irradiation, see:
• 17a Besson T. Fruit C. Synthesis 2016; 48: 3879
• 17b Rathia AK. Gawandea MB. Zborila R. Varmab RS. Coord. Chem. Rev. 2015; 291: 68
• 17c Gupta AK. Singh N. Singh KN. Curr. Org. Chem. 2013; 17: 474
• 17d Sharma A. Vacchani D. Van der Eycken E. Chem. Eur. J. 2013; 19: 1158
• 17e Mehta VP. Van der Eycken E. Chem. Soc. Rev. 2011; 40: 4925
• 17f Baghbanzadeh M. Pilger C. Kappe CO. J. Org. Chem. 2011; 76: 8138
• 18a O’Boyle NM. Bostro J. Sayle RA. Gill A. J. Med. Chem. 2014; 57: 2704
• 18b Topliss JG. J. Med. Chem. 1972; 15: 1006
• 19 Turočkin A. Synthesis 2014; 25: 894
• 20a Guillon R. Pagniez F. Picot C. Hédou D. Tonnerre A. Chosson E. Duflos M. Besson T. Logé C. Le Pape P. ACS Med. Chem. Lett. 2013; 4: 288
• 20b Murakami Y. Watanabe T. Kobayashi A. Yokoyama Y. Synthesis 1984; 738
• 21a Appel R. Janssen H. Siray M. Knoch F. Chem. Ber. 1985; 118: 1632
• 21b English RF. Rakitin OA. Rees CW. Vlasova OG. J. Chem. Soc., Perkin Trans. 1 1997; 201
• 21c Besson T. Rees CW. J. Chem. Soc., Perkin Trans. 1 1995; 1659