Skip to main content
SpringerLink
Log in

Metal-catalyzed synthesis of triazine derivatives

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

Abstract

Heterocycles, primarily the nitrogen-containing six-membered triazines, pyrimidines, and pyridines are used in synthesizing the active pharmaceutical synthons and natural products. Catalysis, particularly transition metal catalysis, can also be used to obtain regioselective, stereoselective, and chemoselective transformations. This review work deals with the recent advances made in metal-mediated/catalyzed synthesis of triazine derivatives and therefore will assist chemists in comprehending the issues associated with the present methods as well as future prospects, in terms of substrate and catalyst respectively. This article is of interest to a large area of organic chemists working in the field of heterocyclic productions in academia and industrial R&D sectors. Noteworthy, this assessment will serve as a guiding light to consider: (i) the importance of several transition metals employed in the method development domain and (ii) in the R&D sector for further necessary modifications.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Suda A, Kawasaki KI, Komiyama S, Isshiki Y, Yoon DO, Kim SJ, Tsukuda T (2014) Bioorg Med Chem 22:892

    Article  CAS  PubMed  Google Scholar 

  2. Klenke B, Stewart M, Barrett MP, Brun R, Gilbert IH (2001) J Med Chem 44:3440

    Article  CAS  PubMed  Google Scholar 

  3. Katritzky AR, Lagowski JM (1995) Synthesis 1995:605

    Article  Google Scholar 

  4. Iino Y, Karakida T, Sugamata N, Andoh T, Takei H, Takahashi M, Morishita Y (1998) Anticancer Res 18:171

    CAS  PubMed  Google Scholar 

  5. Panchal J, Jain S, Jain PK, Kishore D, Dwivedi J (2021) J Heterocycl Chem 58:2049

    Article  CAS  Google Scholar 

  6. Gosalia UA, Jain S, Jain P, Dwivedi J (2020) Res J Pharm Tech 13:5127

    Google Scholar 

  7. Nishimura N, Kato A, Maeba I (2001) Carbohydr Res 331:77

    Article  CAS  PubMed  Google Scholar 

  8. Jain S, Dwivedi J, Jain P, Kishore D (2016) Synth Commun 46:1155

    Article  CAS  Google Scholar 

  9. Hernández-Juárez M, Vaquero M, Álvarez E, Salazar V, Suárez A (2013) Dalton Trans 42:351

    Article  PubMed  Google Scholar 

  10. Balaban AT, Oniciu DC, Katritzky AR (2004) Chem Rev 104:2777

    Article  CAS  PubMed  Google Scholar 

  11. Jain S, Jain PK, Sain S, Kishore D, Dwivedi J (2020) Mini-Rev Org Chem 17:904

    Article  CAS  Google Scholar 

  12. Jain S, Sharma A, Agrawal M, Sharma S, Dwivedi J, Kishore D (2013) J Chem 925439

    Google Scholar 

  13. Zhou C, Min J, Liu Z, Young A, Deshazer H, Gao T, Kallenbach NR (2008) Bioorg Med Chem Lett 18:1308

    Article  CAS  PubMed  Google Scholar 

  14. Dhall E, Sain S, Jain S, Dwivedi J (2018) Mini-Rev Org Chem 15:291

    Article  CAS  Google Scholar 

  15. Pandey VK, Tusi S, Tusi Z, Joshi M, Bajpai S (2004) Acta Pharm 54:1

    CAS  PubMed  Google Scholar 

  16. Kushwaha N, Sharma CS (2020) Mini-Rev Med Chem 20:2104

    Article  CAS  PubMed  Google Scholar 

  17. Singla P, Luxami V, Paul K (2015) Eur J Med Chem 102:39

    Article  CAS  PubMed  Google Scholar 

  18. Dhall E, Jain S, Mishra A, Dwivedi J, Sharma S (2018) J Heterocycl Chem 55:2859

    Article  CAS  Google Scholar 

  19. Shah DR, Modh RP, Chikhalia KH (2014) Future Med Chem 6:463

    Article  CAS  PubMed  Google Scholar 

  20. Kumar R, Kumar N, Roy RK, Singh A (2017) Curr Med Drug Res 1:173

    Google Scholar 

  21. Chandrasekhar A, Sankararaman S (2017) J Org Chem 82:11487

    Article  CAS  PubMed  Google Scholar 

  22. Tai S, Dover EJ, Marchi SV, Carrick JD (2015) J Org Chem 80:6275

    Article  CAS  PubMed  Google Scholar 

  23. Hu QY, Lu WX, Tang HD, Sung HHY, Wen TB, Williams ID, Wong GKL, Lin Z, Jia G (2005) Organometallics 24:3966

    Article  CAS  Google Scholar 

  24. Patel AB, Chikhalia KH, Kumari P (2014) Eur J Med Chem 79:57

    Article  CAS  PubMed  Google Scholar 

  25. Dalvadi JP, Patel PK, Chikhalia KH (2013) RSC Adv 3:8960

    Article  CAS  Google Scholar 

  26. Zhong H, Xu E, Zeng D, Du J, Sun J, Ren S, Fang Q (2008) Org Lett 10:709

    Article  CAS  PubMed  Google Scholar 

  27. Liu XK, Zheng CJ, Xiao J, Ye J, Liu CL, Wang SD, Zhang XH (2012) Phys Chem Chem Phys 14:14255

    Article  CAS  PubMed  Google Scholar 

  28. Zhu Z, Shao E, Xu S, Sun H, Zhang G, Xie Z, Gao Z (2016) RSC Adv 6:76883

    Article  CAS  Google Scholar 

  29. Lipińska T, Branowska D, Rykowski A (1999) Chem Heterocycl Comp 35:334

    Article  Google Scholar 

  30. Branowska D, Olender E, Rykowski A (2014) Tetrahedron 70:4697

    Article  CAS  Google Scholar 

  31. Xu X, Zhang M, Jiang H, Zheng J, Li Y (2014) Org Lett 16:3540

    Article  CAS  PubMed  Google Scholar 

  32. Pawar AB, Chang S (2014) Chem Commun 50:448

    Article  CAS  Google Scholar 

  33. Zhang LY, Zhang C, Wang T, Shi YL, Ban M, Cui DM (2018) J Org Chem 84:536

    Article  CAS  PubMed  Google Scholar 

  34. Ananthnag GS, Mague JT, Balakrishna MS (2015) Inorg Chem 54:10985

    Article  CAS  PubMed  Google Scholar 

  35. Shah DR, Lakum HP, Chikhalia KH (2014) Heterocycl Commun 20:305

    Article  CAS  Google Scholar 

  36. Lin B, Wu W, Weng Z (2019) Tetrahedron 75:2843

    Article  CAS  Google Scholar 

  37. Cassidy MP, Raushel J, Fokin VV (2006) Angew Chem 118:3226

    Article  Google Scholar 

  38. Wu W, Wang J, Wang Y, Huang Y, Tan Y, Weng Z (2017) Angew Chem Int Ed 56:10476

    Article  CAS  Google Scholar 

  39. Weng Z, Lee R, Jia W, Yuan Y, Wang W, Feng X, Huang KW (2011) Organometallics 30:3229

    Article  CAS  Google Scholar 

  40. Jia FC, Xu C, Wang YW, Chen ZP, Chen YF, Wu AX (2018) Org Biomol Chem 16:4223

    Article  CAS  PubMed  Google Scholar 

  41. Ma YG, Li C, Yao CS, Wang XS (2016) Tetrahedron 72:3844

    Article  CAS  Google Scholar 

  42. Yan Y, Cui C, Wang J, Li S, Liu Y (2019) Adv Synth Catal 361:1166

    Article  CAS  Google Scholar 

  43. Yan Y, Li H, Li Z, Niu B, Shi M, Liu Y (2017) J Org Chem 82:8628

    Article  CAS  PubMed  Google Scholar 

  44. Wang M, Meng Y, Wei W, Wu J, Yu W, Chang J (2018) Adv Synth Catal 360:86

    Article  CAS  Google Scholar 

  45. Song L, Tian X, Lv Z, Li E, Wu J, Liu Y, Chang J (2015) J Org Chem 80:7219

    Article  CAS  PubMed  Google Scholar 

  46. Parvatkar PT, Parameswaran PS, Tilve SG (2012) Chem Eur J 18:5460

    Article  CAS  PubMed  Google Scholar 

  47. Shang E, Zhang J, Bai J, Wang Z, Li X, Zhu B, Lei X (2016) Chem Commun 52:7028

    Article  CAS  Google Scholar 

  48. Zhang C, Ban MT, Zhu K, Zhang LY, Luo ZY, Guo SN, Zhang Y (2017) Org Lett 19:3947

    Article  CAS  PubMed  Google Scholar 

  49. Vieira TO, Meaney LA, Shi YL, Alper H (2008) Org Lett 10:4899

    Article  CAS  PubMed  Google Scholar 

  50. Dao P, Garbay C, Chen H (2013) Tetrahedron 69:3867

    Article  CAS  Google Scholar 

  51. Li JJ, Song C, Cui DM, Zhang C (2017) Org Biomol Chem 15:5564

    Article  CAS  PubMed  Google Scholar 

  52. Ueda S, Nagasawa H (2009) J Am Chem Soc 131:15080

    Article  CAS  PubMed  Google Scholar 

  53. Huang H, Guo W, Wu W, Li CJ, Jiang H (2015) Org Lett 17:2894

    Article  CAS  PubMed  Google Scholar 

  54. Ding S, Jiao N (2012) Angew Chem Int Ed 51:9226

    Article  CAS  Google Scholar 

  55. Huang L, Jiang H, Qi C, Liu X (2010) J Am Chem Soc 132:17652

    Article  CAS  PubMed  Google Scholar 

  56. You Q, Wang F, Wu C, Shi T, Min D, Chen H, Zhang W (2015) Org Biomol Chem 13:6723

    Article  CAS  PubMed  Google Scholar 

  57. Debnath P, Majumdar KC (2014) Tetrahedron Lett 55:6976

    Article  CAS  Google Scholar 

  58. Chen J, Liu B, Chen Y, He Q, Yang C (2014) RSC Adv 4:11168

    Article  CAS  Google Scholar 

  59. Ding Q, Li M, Sun Y, Yu Y, Baell JB, Huang F (2020) Org Chem Frontiers 7:457

    Article  CAS  Google Scholar 

  60. Havránková E, Csöllei J, Pazdera P (2009) Molecules 24:3586

    Article  CAS  Google Scholar 

  61. Liao Y, Weber J, Faul CF (2015) Macromolecules 48:2064

    Article  CAS  Google Scholar 

  62. Abdollahi-Alibeik M, Pouriayevali M (2012) Catal Commun 22:13

    Article  CAS  Google Scholar 

  63. Shekouhy M, Moaddeli A, Khalafi-Nezhad A (2017) J Ind Eng Chem 50:41

    Article  CAS  Google Scholar 

  64. Kumari ALS, Swamy KK (2015) J Org Chem 80:4084

    Article  CAS  PubMed  Google Scholar 

  65. Siva Kumari AL, Kumara Swamy KC (2016) J Org Chem 81:1425

    Article  CAS  PubMed  Google Scholar 

  66. Butler RN, Fahy AM, Fox A, Stephens JC, McArdle P, Cunningham D, Ryder A (2006) J Org Chem 71:5679

    Article  CAS  PubMed  Google Scholar 

  67. Zheng Y, Chi Y, Bao M, Qiu L, Xu X (2017) J Org Chem 82:2129

    Article  CAS  PubMed  Google Scholar 

  68. Lei X, Gao M, Tang Y (2016) Org Lett 18:4990

    Article  CAS  PubMed  Google Scholar 

  69. Meng J, Wen M, Zhang S, Pan P, Yu X, Deng WP (2017) J Org Chem 82:1676

    Article  CAS  PubMed  Google Scholar 

  70. Hunt JC, Briggs Clarke ED, Whittingham WG (2007) Bioorg Med Chem Lett 17:5222

    Article  CAS  PubMed  Google Scholar 

  71. Thummel RP, Jahng Y (1986) Inorg Chem 25:2527

    Article  CAS  Google Scholar 

  72. Hanan GS, Arana C, Lehn JM, Baum G, Fenske D (1996) Chem Eur J 2:1292

    Article  CAS  Google Scholar 

  73. Paul P, Tyagi B, Bilakhiya AK, Bhadbhade MM, Suresh E, Ramachandraiah G (1998) Inorg Chem 37:5733

    Article  CAS  Google Scholar 

  74. Geary WJ (1971) Coord Chem Rev 7:81

    Article  CAS  Google Scholar 

  75. Ortmans I, Didier P, Kirsch-De Mesmaeker A (1995) Inorg Chem 34:3695

    Article  CAS  Google Scholar 

  76. Feng JJ, Lin TY, Zhu CZ, Wang H, Wu HH, Zhang J (2016) J Am Chem Soc 138:2178

    Article  CAS  PubMed  Google Scholar 

  77. Zhu CZ, Feng JJ, Zhang J (2017) Chem Commun 53:4688

    Article  CAS  Google Scholar 

  78. Hoang GL, Søholm Halskov K, Ellman JA (2018) J Org Chem 83:9522

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  79. Akao A, Nonoyama N, Yasuda N (2006) Tetrahedron Lett 47:5337

    Article  CAS  Google Scholar 

  80. Nakagawa Y, Suzuki Y, Higashihara T, Ando S, Ueda M (2011) Macromolecules 44:9180

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Authors are thankful to the Vice Chancellor, Banasthali Vidyapith, India, for providing the necessary facilities for the compilation of present work. Besides, Department of Chemistry, Banasthali Vidyapith, is also highly acknowledged for unending support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Banasthali Vidyapith, Banasthali, 304022, India

    Sonika Jain, Jyoti Kumawat,  Shruti, Prerna Malik, Jaya Dwivedi & D. Kishore

  2. Department of Pharmacy, Banasthali Vidyapith, Banasthali, 304022, India

    Pankaj Jain

Authors
  1. Sonika Jain
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jyoti Kumawat
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pankaj Jain
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shruti
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Prerna Malik
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jaya Dwivedi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. D. Kishore
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sonika Jain.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jain, S., Kumawat, J., Jain, P. et al. Metal-catalyzed synthesis of triazine derivatives. Monatsh Chem 153, 517–543 (2022). https://doi.org/10.1007/s00706-022-02948-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-022-02948-2

Keywords

Search

Navigation