Skip to main content
SpringerLink
Log in

Recent progress in the application of amidines for the synthesis of N-heterocyclic compounds

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

Abstract

Nitrogen-containing heterocycles are an inseparable part of many biologically active compounds. Therefore, the synthesis of these structures is of great importance in the field of synthetic chemistry. Due to the presence of two nitrogen atoms in the amidine structure, this molecule can be considered as a dual nucleophile in the synthesis of various heterocycles. The current review highlights recent advances in the application of amidines, in particular, N-arylamidines, as versatile precursors in transition metal-catalyzed, and metal-free reactions for the construction of N-heterocyclic compounds.

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

Similar content being viewed by others

References

  1. Candeias NR, Branco LC, Gois PM, Afonso CA, Trindade AF (2009) Chem Rev 109:2703

    CAS  PubMed  Google Scholar 

  2. Hili R, Yudin AK (2006) Nat Chem Biol 2:284

    CAS  PubMed  Google Scholar 

  3. Draghici C, Wang T, Spiegel DA (2015) Science 350:294

    CAS  PubMed  Google Scholar 

  4. Shiotani S, Kometani T, Mitsuhashi K, Nozawa T, Kurobe A, Futsukaichi O (1976) J Med Chem 19:803

    CAS  PubMed  Google Scholar 

  5. Silva VG, Silva RO, Damasceno SR, Carvalho NS, Prudêncio RS, Aragão KS, Guimarães MA, Campos SA, Véras LM, Godejohann M (2013) J Nat Prod 76:1071

    CAS  PubMed  Google Scholar 

  6. Muñoz J, Köck M (2016) J Nat Prod 79:434

    PubMed  Google Scholar 

  7. Tang W-Z, Yang Z-Z, Wu W, Tang J, Sun F, Wang S-P, Cheng C-W, Yang F, Lin H-W (2018) J Nat Prod 81:894

    CAS  PubMed  Google Scholar 

  8. Joshi H, Upadhyay P, Karia D, Baxi A (2003) Eur J Med Chem 38:837

    CAS  PubMed  Google Scholar 

  9. Kaloumenos NS, Capote N, Aguado A, Eleftherohorinos IG (2013) Pesticide Biochem Physiol 105:177

    CAS  Google Scholar 

  10. Szabó KE, Kyriakis E, Psarra A-MG, Karra AG, Sipos Á, Docsa T, Stravodimos GA, Katsidou E, Skamnaki VT, Liggri PG (2019) J Med Chem 62:6116

  11. Khatun S, Singh A, Bader GN, Sofi FA (2022) J Biomol Struct Dyn 40:14279

    CAS  PubMed  Google Scholar 

  12. Dymińska L (2015) Bioorg Med Chem 23:6087

    PubMed  Google Scholar 

  13. Barden TC (2010) Indoles: Industrial, Agricultural and Over-the-Counter Uses. In: Gribble GW (ed) Heterocyclic scaffolds II: reactions and applications of indoles. Topics in heterocyclic chemistry, vol 26. Springer, Berlin, p 31

    Google Scholar 

  14. Ndagijimana A, Wang X, Pan G, Zhang F, Feng H, Olaleye O (2013) Fitoterapia 86:35

    CAS  PubMed  Google Scholar 

  15. Kumari A, Singh RK (2019) Bioorg Chem 89:103021

    CAS  PubMed  Google Scholar 

  16. Jain K, Chitre T, Miniyar P, Kathiravan M, Bendre V, Veer V, Shahane S, Shishoo C (2006) Curr Sci 90:793

    CAS  Google Scholar 

  17. Jain K, Arya N, Inamdar N, Auti P, Unawane S, Puranik H, Sanap M, Inamke A, Mahale V, Prajapati C (2016) Curr Top Med Chem 16:3133

    CAS  PubMed  Google Scholar 

  18. Selvam TP, James CR, Dniandev PV, Valzita SK (2012) Res Pharm 2:271

    Google Scholar 

  19. Zarenezhad E, Farjam M, Iraji A (2021) J Mol Struct 1230:129833

    CAS  Google Scholar 

  20. Hussaini SMA (2016) Exp Opin Ther Pat 26:1201

    CAS  Google Scholar 

  21. Mukherjee S, Pal M (2013) Curr Med Chem 20:4386

    CAS  PubMed  Google Scholar 

  22. Ajani OO, Iyaye KT, Ademosun OT (2022) RSC Adv 12:18594

    CAS  PubMed  PubMed Central  Google Scholar 

  23. Selvam TP, Kumar PV (2011) Res Pharm 1:204

    Google Scholar 

  24. Hameed A, Al-Rashida M, Uroos M, Ali SA, Arshia IM, Khan KM (2018) Exp Opin Ther Pat 28:281

    CAS  Google Scholar 

  25. Karan R, Agarwal P, Sinha M, Mahato N (2021) Chem Eng 5:73

    CAS  Google Scholar 

  26. Ke S, Cao X, Liang Y, Wang K, Yang Z (2011) Mini Rev Med Chem 11:642

    CAS  PubMed  Google Scholar 

  27. Akbar S, Das S, Iqubal A, Ahmed B (2022) J Biomol Struct Dyn 40:9974

    CAS  PubMed  Google Scholar 

  28. Niu Z-X, Wang Y-T, Zhang S-N, Li Y, Chen X-B, Wang S-Q, Liu H-M (2023) Eur J Med Chem 250:115172

    CAS  PubMed  Google Scholar 

  29. Borcea A-M, Ionuț I, Crișan O, Oniga O (2021) Molecules 26:624

    CAS  PubMed  PubMed Central  Google Scholar 

  30. Angeli A, Trallori E, Ferraroni M, Mannelli LDC, Ghelardini C, Supuran CT (2018) Eur J Med Chem 157:1214

    CAS  PubMed  Google Scholar 

  31. Koketsu M, Ishihara H (2003) Curr Org Chem 7:175

    CAS  Google Scholar 

  32. Stock M, Elazab S, Hsu W (2018) J Vet Pharmacol Ther 41:184

    CAS  PubMed  Google Scholar 

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

    Google Scholar 

  34. Charlson F, Degenhardt L, McLaren J, Hall W, Lynskey M (2009) Pharmacoepidemiol Drug Saf 18:93

    PubMed  Google Scholar 

  35. Li J, John M, Ackermann L (2014) Chem Eur J 20:5403

    CAS  PubMed  Google Scholar 

  36. Xu F, Kang W-F, Wang Y, Liu C-S, Tian J-Y, Zhao R-R, Du M (2018) Org Lett 20:3245

    CAS  PubMed  Google Scholar 

  37. Wang J, Zhang F-D, Tang D, Wu P, Zhang X-G, Chen B-H (2017) RSC Adv 7:24594

    CAS  Google Scholar 

  38. Zhou X, Ma H, Shi C, Zhang Y, Liu X, Huang G (2017) Eur J Org Chem 2017:237

    CAS  Google Scholar 

  39. Qu J, Wu P, Tang D, Meng X, Chen Y, Guo S, Chen B (2015) New J Chem 39:4235

    CAS  Google Scholar 

  40. Vadagaonkar KS, Kalmode HP, Prakash S, Chaskar AC (2015) New J Chem 39:3639

    CAS  Google Scholar 

  41. Zhu Y, Li C, Zhang J, She M, Sun W, Wan K, Wang Y, Yin B, Liu P, Li J (2015) Org Lett 17:3872

    CAS  PubMed  Google Scholar 

  42. Lin M, Chen Q-Z, Zhu Y, Chen X-L, Cai J-J, Pan Y-M, Zhan Z-P (2011) Synlett 2011:1179

    Google Scholar 

  43. Wang C, Wang E, Chen W, Zhang L, Zhan H, Wu Y, Cao H (2017) J Org Chem 82:9144

    CAS  PubMed  Google Scholar 

  44. Wang C, Jiang H, Chen W, Dong J, Chen Z, Cao H (2017) Org Biomol Chem 15:6463

    CAS  PubMed  Google Scholar 

  45. Chen J, Properzi R, Uccello DP, Young JA, Dushin RG, Starr JT (2014) Org Lett 16:4146

    CAS  PubMed  Google Scholar 

  46. Li Y, Qi Z, Wang H, Yang X, Li X (2016) Angew Chem Int Ed 55:11877

    CAS  Google Scholar 

  47. Guo W, Zhao M, Tan W, Zheng L, Tao K, Fan X (2019) Org Chem Front 6:2120

    CAS  Google Scholar 

  48. Li G, He R, Liu Q, Wang Z, Liu Y, Wang Q (2019) J Org Chem 84:8646

    CAS  PubMed  Google Scholar 

  49. Liu W, He J, Liu X, Yu Y, Pei Y, Zhu B, Cao H (2020) J Org Chem 85:14954

    CAS  PubMed  Google Scholar 

  50. Song X, Cai X, Zhang X, Fan X (2021) Org Chem Front 8:6265

    CAS  Google Scholar 

  51. Wu C, Zhou J, He G, Li H, Yang Q, Wang R, Zhou Y, Liu H (2019) Org Chem Front 6:1183

    CAS  Google Scholar 

  52. Xu H-B, Zhu Y-Y, Dong L (2019) J Org Chem 84:16286

    CAS  PubMed  Google Scholar 

  53. Zhou Q, Song X, Zhang X, Fan X (2021) Org Chem Front 8:4131

    CAS  Google Scholar 

  54. Wang C, Yu Y, Su Z, Li X, Cao H (2019) Org Lett 21:4420

    CAS  PubMed  Google Scholar 

  55. Liu W, Zhang Y, He J, Yu Y, Yuan J, Ye X, Zhang Z, Xue L, Cao H (2019) J Org Chem 84:11348

    CAS  PubMed  Google Scholar 

  56. Tian Y, Qin M, Yang X, Zhang X, Liu Y, Guo X, Chen B (2019) Tetrahedron 75:2817

    CAS  Google Scholar 

  57. Lu G, Luo N, Hu F, Ban Z, Zhan Z, Huang GS (2020) Adv Synth Catal 362:487

    CAS  Google Scholar 

  58. Zhan Z, Zhang M, Jiang P, He J, Luo N, Wang H, Wang M, Huang G (2021) Asian J Org Chem 10:1801

    CAS  Google Scholar 

  59. Zhang Y, Wan X, Gan J, Wang C (2021) Synthesis 53:4507

    CAS  Google Scholar 

  60. Xu H, Hong R, Weng M-Y, Huang R-L, Wang G-W, Zhang Z (2021) Org Lett 23:5305

    CAS  PubMed  Google Scholar 

  61. Xu H, Huang R-L, Shu Z, Hong R, Zhang Z (2021) Org Biomol Chem 19:4978

    CAS  PubMed  Google Scholar 

  62. Xu H, Chen H, Hu X, Xuan G, Li P, Zhang Z (2022) J Org Chem 87:16204

    CAS  PubMed  Google Scholar 

  63. Zhao HB, Zhuang JL, Xu HC (2021) Chemsuschem 14:1692

    CAS  PubMed  Google Scholar 

  64. Tang Q, Xu K, He X, Shang Y (2022) Adv Synth Catal 364:4103

    CAS  Google Scholar 

  65. Takeda A, Okai H, Watabe K, Iida H (2022) J Org Chem 87:10372

    CAS  PubMed  Google Scholar 

  66. Liu Z, Zhang YS, Wei Y, Shi M (2020) Eur J Org Chem 2020:1093

    CAS  Google Scholar 

  67. Li W, Xin J, Zhai P, Lin J, Huang S, Gao W, Li X (2021) Org Biomol Chem 19:6473

    CAS  PubMed  Google Scholar 

  68. Liu X, Gao C, Wang M (2022) J Org Chem 87:11274

    CAS  PubMed  Google Scholar 

  69. Wang Q, Xiao F, Huang Z, Mao G, Deng G-J (2023) J Org Chem 88:1963

    CAS  PubMed  Google Scholar 

  70. Zhao R, Yan M, Zhang R, Ma Y, Chen J (2019) ChemSelect 4:10907

    CAS  Google Scholar 

  71. Wang T, Xu L, Dong J (2023) Org Lett 25:6222

    CAS  PubMed  Google Scholar 

  72. Xie H, Xing Q, Shan Z, Xiao F, Deng GJ (2019) Adv Synth Catal 361:1896

    CAS  Google Scholar 

  73. Yang Q, Wu C, Zhou J, He G, Liu H, Zhou Y (2019) Org Chem Front 6:393

    CAS  Google Scholar 

  74. Ren J, Pi C, Cui X, Wu Y (2021) Org Lett 23:6628

    CAS  PubMed  Google Scholar 

  75. Meng YY, Zhu WJ, Song YY, Bu GG, Zhang LJ, Xu F (2021) Eur J Org Chem 2021:1290

    CAS  Google Scholar 

  76. Li Y, Wang H, Li Y, Li Y, Sun Y, Xia C, Li Y (2021) J Org Chem 86:18204

    CAS  PubMed  Google Scholar 

  77. Huang X, Xu Y, Li J, Lai R, Luo Y, Wang Q, Yang Z, Wu Y (2021) Chin Chem Lett 32:3518

    CAS  Google Scholar 

  78. Zhou Q, Song X, Zhang X, Fan X (2022) Org Lett 24:1280

    CAS  PubMed  Google Scholar 

  79. Sankaram GS, Sahoo T, Sridhar B, Reddy BS (2023) Org Biomol Chem 21:1719

    CAS  PubMed  Google Scholar 

  80. Hu F, Cui X, Ban Z, Lu G, Luo N, Huang G (2019) Org Biomol Chem 17:2356

    CAS  PubMed  Google Scholar 

  81. Ren J, Huang Y, Pi C, Cui X, Wu Y (2021) Chin Chem Lett 32:2592

    CAS  Google Scholar 

  82. Wang C, Fan X, Chen F, Qian P-C, Cheng J (2021) Chem Commun 57:3929

    CAS  Google Scholar 

  83. Charpe VP, Ragupathi A, Sagadevan A, Hwang KC (2021) Green Chem 23:5024

    CAS  Google Scholar 

  84. Zhang Y, Kuang J, Xiao X, Wang L, Ma Y (2021) Org Lett 23:3960

    CAS  PubMed  Google Scholar 

  85. Yan M, Ma R, Chen R, Wang L, Wang Z, Ma Y (2020) Chem Commun 56:10946

    CAS  Google Scholar 

  86. Poly SS, Hashiguchi Y, Nakamura I, Fujitani T, Siddiki SH (2022) Catal Sci Technol 12:4679

    CAS  Google Scholar 

  87. Guo H, Lin J, Liu Q, Li X (2023) Org Biomol Chem 21:4269

    CAS  PubMed  Google Scholar 

  88. Wu Q, Li L, Xu B, Sun J, Ji D, Li Y, Shen L, Fang Z, Duan J, Chen B (2023) Green Synth Catal 4:150

    Google Scholar 

  89. Anantoju KK, Eppkayala L, Maringanti TC (2019) Asian J Chem 31:845

    CAS  Google Scholar 

  90. Sun L-W, Yu Z-L, Luo X-L, Ma M, Shen Z-L, Chu X-Q (2022) Org Chem Front 9:109

    CAS  Google Scholar 

  91. Liu J, Zhuo J, Tan Q, Zhou M, Ma L, Zhang M (2023) Org Biomol Chem 21:3411

    CAS  PubMed  Google Scholar 

  92. Wu Z-C, Houk K, Boger DL, Svatunek D (2022) J Am Chem Soc 144:10921

    CAS  PubMed  PubMed Central  Google Scholar 

  93. Li J, Tang M, Zang L, Zhang X, Zhang Z, Ackermann L (2016) Org Lett 18:2742

    CAS  PubMed  Google Scholar 

  94. Xu S, Qiao S, Sun S, Yu J-T, Cheng J (2019) Org Biomol Chem 17:8417

    CAS  PubMed  Google Scholar 

  95. Xu L, Wang L, Feng Y, Li Y, Yang L, Cui X (2017) Org Lett 19:4343

    CAS  PubMed  Google Scholar 

  96. Zhou J, Li J, Li Y, Wu C, He G, Yang Q, Zhou Y, Liu H (2018) Org Lett 20:7645

    CAS  PubMed  Google Scholar 

  97. Li Y, Jia C, Li H, Xu L, Wang L, Cui X (2018) Org Lett 20:4930

    CAS  PubMed  Google Scholar 

  98. Lai R, Wu X, Lv S, Zhang C, He M, Chen Y, Wang Q, Hai L, Wu Y (2019) Chem Commun 55:4039

    CAS  Google Scholar 

  99. Zhou X, Qi Z, Yu S, Kong L, Li Y, Tian WF, Li X (2017) Adv Synth Catal 359:1620

    CAS  Google Scholar 

  100. Song X, Zhou Q, Zhao J, Jiang Y, Zhang X, Zhang X, Fan X (2020) Org Lett 22:9506

    CAS  PubMed  Google Scholar 

  101. Zhang LL, Cao WB, Xu XP, Ji SJ (2019) Org Chem Front 6:1787

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

    Fatemeh Doraghi, Mehdi Ghanbarlou, Bagher Larijani & Mohammad Mahdavi

  2. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

    Somaye Karimian

  3. School of Chemistry, College of Science, University of Tehran, Tehran, Iran

    Hamed Navid

Authors
  1. Fatemeh Doraghi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Somaye Karimian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hamed Navid
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mehdi Ghanbarlou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bagher Larijani
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Mohammad Mahdavi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Mahdavi.

Additional information

Publisher's Note

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

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Doraghi, F., Karimian, S., Navid, H. et al. Recent progress in the application of amidines for the synthesis of N-heterocyclic compounds. Monatsh Chem 155, 419–439 (2024). https://doi.org/10.1007/s00706-024-03180-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-024-03180-w

Keywords

Search

Navigation