Skip to main content

Advertisement

Log in

An efficient and convenient protocol for the synthesis of diaminotriarylmethanes

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A novel and efficient procedure was developed for the preparation of diaminotriarylmethanes through the Baeyer condensation of aromatic aldehydes and N,N-dimethylaniline or N,N-diethylaniline in the presence of niobium chloride under solvent-free conditions. This approach offers several advantages, such as short reaction time, high yields, low cost, and mild reaction conditions.

Graphical abstract

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

Similar content being viewed by others

References

  1. Duxbury DF (1993) Chem Rev 93:381

    Article  CAS  Google Scholar 

  2. Nair V, Thomas S, Mathew SC, Abhilash KG (2006) Tetrahedron 62:6731

    Article  CAS  Google Scholar 

  3. Sanguinet L, Twieg RJ, Wiggers G, Mao GL, Singer KD, Petschek RG (2005) Tetrahedron Lett 46:5121

    Article  CAS  Google Scholar 

  4. Al-Qawasmeh RA, Lee Y, Cao MY, Gu XP, Vassilakos A, Wright JA, Young A (2004) Bioorg Med Chem Lett 14:347

    Article  CAS  Google Scholar 

  5. Jafarpour F, Bardajee GR, Pirelahi H, Oroojpour V, Dehnamaki H, Rahmdel S (2009) Chin J Chem 27:1415

    Article  CAS  Google Scholar 

  6. Guzman-Lucero D, Guzman J, Likhatchev D, Martinez-Palou R (2005) Tetrahedron Lett 46:1119

    Article  CAS  Google Scholar 

  7. Yan SL, Gao ZX, Fang YJ, Cheng YY, Zhou HY, Wang HY (2007) Dyes Pigm 74:572

    Article  CAS  Google Scholar 

  8. Esquivias J, Arrayas RG, Carretero JC (2006) Angew Chem Int Ed 45:629

    Article  CAS  Google Scholar 

  9. Genovese S, Epifano F, Pelucchini C, Curini M (2009) Eur J Org Chem 1132

  10. Thirupathi P, Kim SS (2010) Eur J Org Chem 1798

  11. Prakash GKS, Panja C, Shakhmin A, Shah E, Mathew T, Olah GA (2009) J Org Chem 74:8659

    Article  CAS  Google Scholar 

  12. Khera RA, Ullah I, Ahmad R, Riahi A, Hung NTH, Sher M, Villinger A, Fischer C, Langer P (2010) Tetrahedron 66:1643

    Article  CAS  Google Scholar 

  13. Kodomari M, Nagamatsu M, Akaike M, Aoyama T (2008) Tetrahedron Lett 49:2537

    Article  CAS  Google Scholar 

  14. Leng YX, Chen F, Zuo L, Duan WH (2010) Tetrahedron Lett 51:2370

    Article  CAS  Google Scholar 

  15. Pratt EF, Green LQ (1953) J Am Chem Soc 75:275

    Article  CAS  Google Scholar 

  16. Khosropour AR, Esmaeilpoor K, Moradie A (2006) J Iran Chem Soc 3:81

    CAS  Google Scholar 

  17. An LT, Ding FQ, Zou HP (2008) Dyes Pigm 77:478

    Article  CAS  Google Scholar 

  18. Shanmuga P, Varma L (2001) Indian J Chem 40B:1258

    CAS  Google Scholar 

  19. Zhang ZH, Yang F, Li TS, Fu CG (1997) Synth Commun 27:3823

    Article  CAS  Google Scholar 

  20. Paul AM, Khandekar AC, Khadilkar BM (2003) J Chem Res 168

  21. Wang R, Li BG, Huang TK, Shi L, Lu XX (2007) Tetrahedron Lett 48:2071

    Article  CAS  Google Scholar 

  22. Heravi MM, Nahavandi F, Sadjadi S, Oskooie HA, Tajbakhsh M (2009) Synth Commun 39:3285

    Article  CAS  Google Scholar 

  23. Gao ST, Zhao Y, Li C, Ma JJ, Wang C (2009) Synth Commun 39:2221

    Article  CAS  Google Scholar 

  24. Gao ST, Liu WH, Ma JJ, Wang C, Liang Q (2009) Synth Commun 39:3278

    Article  CAS  Google Scholar 

  25. Majhi A, Kim SS, Kim HS (2008) Appl Organomet Chem 22:466

    Article  CAS  Google Scholar 

  26. Yadav JS, Bhunia DC, Singh VK, Srihari P (2009) Tetrahedron Lett 50:2470

    Article  CAS  Google Scholar 

  27. Hou JT, Liu YH, Zhang ZH (2010) J Heterocycl Chem 47:703

    CAS  Google Scholar 

  28. Hou JT, Gao JW, Zhang ZH (2011) Appl Organomet Chem 25:47

    Article  CAS  Google Scholar 

  29. Liu YH, Liu QS, Zhang ZH (2008) J Mol Catal A Chem 296:42

    Article  CAS  Google Scholar 

  30. Liu YH, Zhang ZH, Li TS (2008) Synthesis 3314

  31. Liu YH, Liu QS, Zhang ZH (2009) Tetrahedron Lett 50:916

    Article  CAS  Google Scholar 

  32. Liu HY, Yang SH, Gao JW, Zhang ZH (2010) J Comb Chem 12:643

    Article  Google Scholar 

  33. Zhang ZH, Wang HJ, Ren XQ, Zhang YY (2009) Monatsh Chem 140:1481

    Article  CAS  Google Scholar 

  34. Zhang P, Zhang ZH (2009) Monatsh Chem 140:199

    Article  CAS  Google Scholar 

  35. Wang HJ, Lu J, Zhang ZH (2010) Monatsh Chem 141:1107

    Article  CAS  Google Scholar 

  36. Wang HJ, Zhang XN, Zhang ZH (2010) Monatsh Chem 141:425

    Article  CAS  Google Scholar 

  37. Coghlan MJ, Luly JR, Schkeryantz JM, Wang AX (2000) PCT WO/2000/006137

  38. Reddy CS, Nagaraj A, Srinivas A, Reddy GP (2009) Indian J Chem 48B:248

    Google Scholar 

  39. Fox BM, Hepworth JD, Mason D, Sawyer J, Hallas G (1982) J Soc Dyers Colour 98:10

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are thankful to the National Natural Science Foundation of China (20872025 and 21072042) and the Nature Science Foundation of Hebei Province (B2008000149) for financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhan-Hui Zhang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hou, JT., Gao, JW. & Zhang, ZH. An efficient and convenient protocol for the synthesis of diaminotriarylmethanes. Monatsh Chem 142, 495–499 (2011). https://doi.org/10.1007/s00706-011-0461-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0461-2

Keywords

Navigation