Synthesis 2017; 49(20): 4615-4622
DOI: 10.1055/s-0036-1588434
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Florence Couly
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France   Email: corinne.fruit@univ-rouen.fr   Email: thierry.besson@univ-rouen.fr
,
Carole Dubouilh-Benard
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France   Email: corinne.fruit@univ-rouen.fr   Email: thierry.besson@univ-rouen.fr
,
Thierry Besson*
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France   Email: corinne.fruit@univ-rouen.fr   Email: thierry.besson@univ-rouen.fr
,
Corinne Fruit*
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France   Email: corinne.fruit@univ-rouen.fr   Email: thierry.besson@univ-rouen.fr
› Author Affiliations
Further Information

Publication History

Received: 01 March 2017

Accepted after revision: 02 May 2017

Publication Date:
12 June 2017 (online)

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.

Supporting Information

 
  • 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
  • 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
    • 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