Skip to main content
Log in

Dithiocarbamate promoted practical synthesis of N-Aryl-2-aminobenzazoles: Synthesis of novel Aurora-A kinase inhibitor

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Various N-aryl-2-aminobenzoxazoles and N-aryl-2-aminobenzothiazoles were synthesized from o-aminophenol and o-aminothiophenol, respectively, mediated by dithiocarbamate in one step. The salient features of this method include mild reaction condition, high yield and large scale synthesis. Application of this methodology has been demonstrated by synthesizing potent Aurora kinase-A inhibitors.

Various N-aryl-2-aminobenzoxazoles and N-aryl-2-aminobenzothiazoles were synthesized from o-aminophenol and o-aminothiophenol, respectively, mediated by dithiocarbamate in one step. Application of this methodology has been demonstrated by synthesizing potent Aurora kinase-A inhibitors.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 1

Similar content being viewed by others

References

  1. (a) Harris N V and Fenton G 2002 World Pat. 2002098426; (b) Darque A, Dumetre A, Hutter S, Casano G, Robin M, Pannecouque C and Azas N 2009 Bioorg. Med. Chem. Lett. 19 5962

  2. Martin R E, Mohr P, Maerki H P, Guba W, Kuratli C, Gavelle O, Binggeli A, Bendels S, Alvarez-Sanchez R, Alker A, Polonchuk L and Christ A D 2009 Bioorg. Med. Chem. Lett. 19 6106

  3. (a) Muro F, Limura S, Yoneda Y, Chiba J, Watanabe T, Masaki S, Takayama G, Yokoyama M, Takashi T, Nakayama A and Machinaga N 2009 Bioorg. Med. Chem. 17 1232; (b) Song H, Oh S R, Lee H K, Han G, Kim J H, Chang H W, Doh K E, Rhee H K and Choo Y P 2010 Bioorg. Med. Chem. 18 7580

  4. Potashman M H, Bready J, Coxon A, DeMelfi Jr. T M, DiPietro L, Doerr N, Elbaum D, Estrada J, Gallant P, Germain J, Gu Y, Harmange J C, Kaufman S A, Kendell R, Kim J L, Kumar G N, Long A M, Neervannan S, Patel V F, Polverino A, Rose P, Plas S ven der, Douglas W, Zanon R and Zhao H 2007 J. Med. Chem. 50 4351

  5. Das J, Moquin R V, Lin J, Doweyko H M, Defex H F, Fung Q, Pang S, Pitt S, Shen D R, Schieven G L, Barrish J C and Wityak J 2003 Bioorg. Med. Chem. Lett. 13 2587

  6. Liu C, Lin J, Pitt S, Zhang R F, Sack J S, Kieter S E, Kish K, Doweyko A M, Zhang H, Marathe P H, Trzaskos J, Mckinnon M, Dodd J H, Barrish J C, Schieven G L and Lefthenis K 2008 Bioorg. Med. Chem. Lett. 18 1874

  7. Carpenter R D, Andrei M, Aina O H, Lau H Y, Lightstone F C, Liu R, Lam K S and Kurth M J 2009 J. Med. Chem. 52 14

  8. (a) Ozaki S 1972 Chem Rev. 72 457; (b) Ogura H, Mineo S and Nakagawa K 1981 Chem. Pharm. Bull. 29 1518; (c) Tian Z, Plata D J, Wittenberger S J and Bhatia A V 2005 Tetrahedron Lett. 46 8341

  9. Qian X H, Li Z B, Song G H and Li Z 2001 J. Chem. Res. Synop. 4 138

  10. Ogura H, Mineo S and Nakagawa K 1981 Chem. Pharm. Bull. 29 1518

  11. Cee V J and Downing N S 2006 Tetrahedron Lett. 47 3747

  12. Yella R and Patel B K 2010 J. Comb. Chem. 12 754

  13. (a) Qui J W, Zhang X G, Tang R Y, Zhong P and Li J H 2009 Ad. Synth. Catal. 351 2319; (b) Wang J, Peng F, Jiang J L, Lu Z J, Wang L Y, Bai J and Pan Y 2008 Tetrahedron Lett. 49 467; (c) Joyce L L, Evindar G and Batey R A 2004 Chem. Comm. 446; (d) Benedı C, Bravo F, Uriz P, Fernández E, Claver C and Castillón S 2003 Tetrahedron Lett. 44 6073

  14. Joyce L L and Batey R A 2009 Org. Lett. 11 2792

  15. (a) Das P, Kirankumar C, Nareshkumar K, Innus Md, Iqbal J and Srinivas N 2008 Tetrehedron Lett. 49 922; (b) Nareshkumar K, Sreeramamurthy K, Sandananda P, Mukkanti K and Das P 2010 Tetrahedron Lett. 51 899

  16. (a) Azizi N, Ebrahimi F, Aakbari E, Aryansab F and Saidi M R 2007 Synthesis 2797; (b) Azizi N, Aryanasab F, Torkiyan L, Ziyaei A and Saidi M R 2006 J. Org. Chem. 71 3634; (c) Azizi N, Aryanasab F and Saidi M R 2006 Org. Lett. 8 5275; (d) Wang Y Q, Ge Z M,Hou X L, Cheng T M and Li R T 2004 Synthesis 675; (e) Salvatore R N, Sahab S and Jung K 2001 Tetrahedron Lett. 42 2055

  17. (a) Ple P A, Green T P, Hennequin L F, Curwen J, Fennel M, Allen J, van der Brempt C L and Costello G 2004 J. Med. Chem. 47 871; (b) Sreeramamurthy K, Ashok E, Mahendar V, Santoshkumar G and Das P 2010 Synlett. 721

  18. Pollard J R and Mortimore M 2009 J. Med. Chem. 52 2629

Download references

Acknowledgments

The authors are very thankful to analytical department of Dr. Reddy’s Laboratories Ltd. for the spectral and analytical data.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to NARESH KUMAR KATARI.

Additional information

Supplementary Information

NMR, IR and mass spectra of the synthesized compounds are reported in Supplementary Information available at www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOC 15.0 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

KATARI, N.K., VENKATANARAYANA, M. & SRINIVAS, K. Dithiocarbamate promoted practical synthesis of N-Aryl-2-aminobenzazoles: Synthesis of novel Aurora-A kinase inhibitor. J Chem Sci 127, 447–453 (2015). https://doi.org/10.1007/s12039-015-0803-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-015-0803-4

Keywords

Navigation