Synlett 2014; 25(09): 1279-1282
DOI: 10.1055/s-0033-1341159
letter
© Georg Thieme Verlag Stuttgart · New York

Study of Oxidative Cyclization Using PhI(OAc)2 in the Formation of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and Related Heterocycles – Scope and Limitations

Charles S. Demmer*
a  Medicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark
b  Chemical Neuroscience Group, Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark   Email: charles.demmer@sund.ku.dk   Email: cdemmer15@gmail.com
,
Morten Jørgensen
a  Medicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark
,
Jan Kehler
a  Medicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark
,
Lennart Bunch
b  Chemical Neuroscience Group, Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark   Email: charles.demmer@sund.ku.dk   Email: cdemmer15@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 14 March 2014

Accepted: 19 March 2014

Publication Date:
28 April 2014 (online)

Abstract

A one-pot, two-step reaction for the synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and related heterocycles under mild conditions was herein developed. The key step of this transformation is an oxidative cyclization employing PhI(OAc)2 as reagent. Scope and limitations (group functionality tolerance and sterics) were studied showing the robustness of the present methodology which can be used as potential access to new fused heterocycle libraries.

Supporting Information

 
  • References

  • 2 Demmer CS, Hansen JC, Kehler J, Bunch L. Adv. Synth. Catal. 2014; 356: 1047
    • 3a Hao G.-F, Wang F, Li H, Zhu X.-L, Yang W.-C, Huang L.-S, Wu J.-W, Berry EA, Yang G.-F. J. Am. Chem. Soc. 2012; 134: 11168
    • 3b Trapani G, Franco M, Latrofa A, Carotti A, Gerichi G, Serra M, Biggio G, Liso G. J. Med. Chem. 1996; 31: 575
  • 4 Aboelmagd A, Ali IA. I, Salem EM. S, Abdel-Razik M. Eur. J. Med. Chem. 2013; 60: 503
  • 5 Satyendra RV, Vishnumurthy KA, Vagdevi HM, Rajesh KP, Manjunatha H, Shruthi A. Eur. J. Med. Chem. 2011; 46: 3078
  • 6 Singh G. Synth. Commun. 1994; 24: 2627
    • 7a Deshmukh MB, Patil SS, Jadhav SD, Shejwal RV. Indian J. Heterocycl. Chem. 2010; 20: 163
    • 7b Bhagat TM, Deshmukh SK, Kuberkar SV. J. Heterocycl. Chem. 2012; 49: 873
  • 8 Deshmukh MV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1998; 37: 921
  • 9 Singh G. Synth. Commun. 1994; 24: 2627
  • 10 Butler RN, O’Sullivan P, Scott FL. J. Chem. Soc. C 1971; 2265
    • 11a Aggarwal R, Sumran G. Synth. Commun. 2006; 36: 1873
    • 11b Kumar D, Chandra Sekhar KV. G, Dhillon H, Rao VS, Varma RS. Green Chem. 2004; 6: 156
    • 11c Jørgensen M, Bruun AT, Rasmussen LK. WO 2013034758 A1, 2013
    • 11d Jørgensen M, Bruun AT, Rasmussen LK. WO 2013034755, 2013
    • 12a Mathias JP, Millan DS, Lewthwaite RA, Phillips C. US 200635922 A1, 2006
    • 12b Padalkar VS, Patil VS, Phatangare KR, Sekar N, Umape PG. Synth. Commun. 2011; 41: 925
    • 13a Bhardwaj V, Kumar R, Prakash O, Aneja KR, Tyagi P. Eur. J. Med. Chem. 2004; 39: 1073
    • 13b Collazo AM. G, Pevarello P, Salgado A, Varela C, Garcia F, Alkorta I, Elguero J. J. Mol. Struct. 2011; 987: 13
    • 13c Collazo AM. G, Pevarello P, Salgado A, Varela C. Magn. Reson. Chem. 2010; 48: 614
  • 14 Prakash O, Saini RK, Kumar D, Singh SP. Synth. Commun. 1995; 25: 3363