Synthesis 2016; 48(05): 687-696
DOI: 10.1055/s-0035-1560395
paper
© Georg Thieme Verlag Stuttgart · New York

Metal-Free Oxidative Deamination Cross-Coupling of Imidazo­heterocycles with 2-Aminobenzothiazoles

Xiao-Ming Ji
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China
b   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: rytang@scau.edu.cn
,
Li Xu
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China
,
Yun Yan
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China
,
Fan Chen
b   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: rytang@scau.edu.cn
,
Ri-Yuan Tang*
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 22 October 2015

Accepted after revision: 11 December 2015

Publication Date:
05 January 2016 (online)


Abstract

A metal-free oxidative deamination–cross-coupling of imidazoheterocycles with 2-aminobenzothiazoles in the presence of tert-butyl nitrite is reported for the first time. This simple protocol tolerates a wide range of functional groups to afford various benzothiazole–imidazoheterocycles in moderate to excellent yields, with the release of nitrogen and water as benign byproducts.

Supporting Information

 
  • References

    • 1a Enguehard-Gueiffier C, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
    • 1b Couty F, Evano G In Comprehensive Heterocyclic Chemistry III . Vol.11. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier Science; Oxford: 2008. Chap 11.10; 409 , and references therein
    • 2a Barradas JS, Errea MI, D’Accorso NB, Sepúlveda CS, Damonte EB. Eur. J. Med. Chem. 2010; 46: 259
    • 2b Juspin T, Laget M, Terme T, Azas N, Vanelle P. Eur. J. Med. Chem. 2010; 45: 840
  • 3 Ali A, Cablewski T, Francis CL, Ganguly AK, Sargent RM, Sawutz DG, Winzenberg KN. Bioorg. Med. Chem. Lett. 2011; 21: 4160

    • For selected references, see:
    • 4a Park J.-H, El-Gamal MI, Lee YS, Oh C.-H. Eur. J. Med. Chem. 2011; 46: 5769
    • 4b Ali AR, El-Bendary ER, Ghaly MA, Shehata IA. Eur. J. Med. Chem. 2014; 75: 492
  • 5 Budriesi R, Ioan P, Leoni A, Pedemonte N, Locatelli A, Micucci M, Chiarini A, Galietta LJ. V. J. Med. Chem. 2011; 54: 3885
    • 6a Shao N, Pang G.-X, Yan C.-X, Shi G.-F, Cheng Y. J. Org. Chem. 2011; 76: 7458
    • 6b Stasyuk AJ, Banasiewicz M, Cyrański MK, Gryko DT. J. Org. Chem. 2012; 77: 5552

      For references on imidazo[2,1-b]thiazoles, see:
    • 7a Kolavi G, Hegde V, Khazi AI. Tetrahedron Lett. 2006; 47: 2811
    • 7b Huang G, Sun H, Qiu X, Jin C, Lin C, Shen Y, Jiang J, Wang L. Org. Lett. 2011; 13: 5224
    • 7c Mukherjee C, Watanabe KT, Biehl ER. Tetrahedron Lett. 2012; 53: 6008
  • 8 For reviews on functionalization of imidazo[1,2-a]pyridines, see: Koubachi J, El Kazzouli S, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119; and references cited therein

    • For selected references on C–H arylation of imidazoheterocycles, see:
    • 9a Koubachi J, El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Synlett 2006; 3237
    • 9b Touré BB, Lane BS, Sames D. Org. Lett. 2006; 8: 1979
    • 9c Aginagalde M, Vara Y, Arrieta A, Zangi RV, Cebolla L, Delgado-Camón A, Cossio FP. J. Org. Chem. 2010; 75: 2776
    • 9d Cao H, Zhan H, Lin Y, Lin X.-L, Du Z, Jiang H. Org. Lett. 2012; 14: 1688
    • 9e Fu HY, Chen L, Doucet H. J. Org. Chem. 2012; 77: 4473
    • 9f Lee J, Chung J, Byun SM, Kim BM, Lee C. Tetrahedron 2013; 69: 5660
    • 9g Ke C.-H, Kuo B.-C, Nandi D, Lee HM. Organometallics 2013; 32: 4775
    • 9h Wang S, Liu W, Cen J, Liao J, Huang J, Zhan H. Tetrahedron Lett. 2014; 55: 1589
    • 9i Zhao L, Zhan H, Liao J, Huang J, Chen Q, Qiu H, Cao H. Catal. Commun. 2014; 56: 65
    • 9j Huang S, Qing J, Wang S, Wang H, Zhang L, Tang Y. Org. Biomol. Chem. 2014; 12: 2344

      For reviews on benzothiazole-based drugs, see:
    • 10a Raju GN, Sai KB, Chandana K, Rao NR. J. Chem. Pharm. Res. 2015; 7(4): 286
    • 10b Hroch L, Aitken L, Benek O, Dolezal M, Kuca K, Gunn-Moore F, Musilek K. Curr. Med. Chem. 2015; 22: 730
    • 10c Keri RS, Patil MR, Patil SA, Budagumpi S. Eur. J. Med. Chem. 2015; 89: 207

      For reviews on benzothiazole-based materials, see:
    • 11a Kang E, Kim K, Kim D.-E, Shin H.-K, Lee B.-J. Sci. Adv. Mater. 2014; 6: 2298
    • 11b Xiao GY, Wang Y, Chi HJ, Lu YH, Xu YQ, Hu JY, Hu ZZ, Sun QB. Adv. Mater. Res. 2014; 1033–1034: 342 ; DOI: 10.4028/www.scientific.net/AMR.1033-1034.342
    • 11c Ambrico M, Della Vecchia NF, Ambrico PF, Cardone A, Cicco SR, Ligonzo T, Avolio R, Napolitano A, d’Ischia M. Adv. Funct. Mater. 2014; 24: 7161
    • 11d Conceição DS, Ferreira DP, Graça VC, Silva CR, Santos PF, Vieira Ferreira LF. Tetrahedron 2015; 71: 967

      For selected references on metal-catalyzed C–H activation of benzothiazoles, see:
    • 12a Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 7316
    • 12b Ranjit S, Lee R, Heryadi D, Shen C, Wu J.-E, Zhang P, Huang K.-W, Liu X. J. Org. Chem. 2011; 76: 8999
    • 12c Chu L, Qing F.-L. J. Am. Chem. Soc. 2012; 134: 1298
    • 12d Yu D, Lu L, Shen Q. Org. Lett. 2013; 15: 940
    • 12e Zhao W.-M, Chen X.-L, Yuan J.-W, Qu L.-B, Duan L.-K, Zhao Y.-F. Chem. Commun. 2014; 50: 2018
    • 12f Zhu F, Wang Z.-X. Org. Lett. 2015; 17: 1601

      For selected references on C–H functionalization of benzothiazoles by a free-radical procedure, see:
    • 13a He T, Yu L, Zhang L, Wang L, Wang M. Org. Lett. 2011; 13: 5016
    • 13b Wang J, Wang S, Wang G, Zhang J, Yu X.-Q. Chem. Commun. 2012; 48: 11769
    • 13c Xie Z, Cai Y, Hu H, Lin C, Jiang J, Chen Z, Wang L, Pan Y. Org. Lett. 2013; 15: 4600
    • 13d Liu Y, Jiang B, Zhang W, Xu Z. J. Org. Chem. 2013; 78: 966
    • 13e Chen X.-L, Li X, Qu L.-B, Tang Y.-C, Mai W.-P, Wei D.-H, Bi W.-Z, Duan L.-K, Sun K, Chen J.-Y, Ke D.-D, Zhao Y.-F. J. Org. Chem. 2014; 79: 8407
  • 14 Anastas PT. W, Warner JC. Green Chemistry: Theory and Practice . Oxford University Press; Oxford: 1998
    • 15a Lee YM, Moon ME, Vajpayee V, Filimonov VD, Chi K.-W. Tetrahedron 2010; 66: 7418
    • 15b Bayarmagnai B, Matheis C, Risto E, Goossen JL. Adv. Synth. Catal. 2014; 356: 2343

      For selected references, see:
    • 16a Mo F, Jiang Y, Qiu D, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 1846
    • 16b Fabrizi G, Goggiamani A, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2010; 49: 4067
    • 16c Wu X.-F, Neumann H, Beller M. Angew. Chem. Int. Ed. 2011; 50: 11142
    • 16d Le Callonnec F, Fouquet E, Felpin F.-X. Org. Lett. 2011; 13: 2646
    • 16e Qiu D, Meng H, Jin L, Wang S, Tang S, Wang X, Mo F, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2013; 52: 11581
    • 16f Wang X, Xu Y, Mo F, Ji G, Qiu D, Feng J, Ye Y, Zhang S, Zhang Y, Wang J. J. Am. Chem. Soc. 2013; 135: 10330
    • 16g Wang X, Cuny G, Noël T. Angew. Chem. Int. Ed. 2013; 52: 7860
    • 16h Xia Z, Huang J, He Y, Zhao J, Lei J, Zhu Q. Org. Lett. 2014; 16: 2546

      For selected references on the Meerwein arylation, see:
    • 17a Heinrich MR. Chem. Eur. J. 2009; 15: 820
    • 17b Hari DP, König B. Angew. Chem. Int. Ed. 2013; 52: 4734
    • 17c Hari DP, Schroll P, König B. J. Am. Chem. Soc. 2012; 134: 2958
    • 17d Honraedt A, Raux M.-A, Le Grognec E, Jacquemin D, Felpin F.-X. Chem. Commun. 2014; 50: 5236
    • 17e Crisóstomo FP, Martín T, Carrillo R. Angew. Chem. Int. Ed. 2014; 53: 2181