Multicomponent Synthetic Reactions involving Aminopyrazole-Based Hetrocycles

Authors

  • Rohit Kumar*, Jitendra Kumar Chaurasiyaa, Shachi Tiwaria

Keywords:

Multicomponent reactions, aminopyrazoles, pyrazole-fused heterocycles, aza-heterocycles, 1,3-binucleophiles, heterocyclic synthesis, fused heterocyclic systems, one-pot synthesis, green chemistry, medicinal chemistry

Abstract

Aminopyrazoles are important and versatile building blocks in heterocyclic chemistry and have been extensively employed in the synthesis of pyrazole-fused heterocyclic frameworks. Owing to the presence of multiple reactive sites, aminopyrazoles exhibit diverse chemical reactivity, making them particularly suitable substrates for multicomponent reactions (MCRs). These reactions provide efficient, atom-economical, and sustainable approaches for the rapid construction of structurally complex and functionalized aza-heterocycles. In recent years, the use of aminopyrazoles in MCRs has gained significant attention due to their ability to generate molecular diversity through one-pot processes while minimizing reaction steps, time, and waste. Pyrazole-containing compounds are widely recognized for their medicinal relevance, with reported biological activities including anticancer, antimicrobial, anti-inflammatory, and antiviral properties. Consequently, aminopyrazole-based MCRs have become an attractive strategy for the development of biologically relevant heterocyclic scaffolds. Although several reviews have focused on the synthesis and general applications of aminopyrazoles, a comprehensive review dedicated exclusively to their reactivity in multicomponent reactions has not been reported to date. This review presents a systematic and critical overview of the reactivity of aminopyrazoles in multicomponent reactions, covering various reaction types, mechanistic aspects, and synthetic outcomes. Recent developments, representative examples, and potential future directions in this rapidly evolving area are also highlighted, providing a valuable resource for researchers working in heterocyclic and medicinal chemistry.

References

(a) J. V. Faria, P. F. Vegi, A. G. C. Miguita, M. S. d. Santos, N. Boechat and A. M. R. Bernardino, Bioorg. Med. Chem., 2017, 25, 5891–5903.

(b) M. Lefoix, G. Mathis, T. Kleinmann, J. C. Truffert and U. Asseline, J. Org. Chem., 2014, 79, 3221–3227.

(c) H. de Mello, A. Echevarria, A. M. Bernardino, M. C. Cavalheiro and L. L. Leon, J. Med. Chem., 2004, 47, 5427–5432.

(a) M. F. Khan, M. M. Alam, G. Verma, W. Akhter, and M. Shaquiquzzaman, Eur. J. Med. Chem., 2016, 120, 170–201.

(b) F. E. Bennani, L. Doudach, Y. Cherrah, Y. Ramli, M. Ansar, and M. E. A. Faouzi, Bioorg. Chem., 2020, 97, 103470.

(a) R. Aggarwal and S. Kumar, Beilstein J. Org. Chem., 2018, 14, 203–242.

(b) A. Shaabani, M. T. Nazeri, and R. Afshari, Mol. Divers., 2019, 23, 751–807.

(c) M. Marinozzi, G. Marcelli and A. Carotti, Mini Rev. Med. Chem., 2015, 15, 272–299.

A. Dömling, W. Wang, and K. Wang, Chem. Rev., 2012, 112, 3083–3135.

A. Tigreros and J. Portilla, RSC Adv., 2020, 10, 19693–19712.

C.-H. Chen, F.-I. Wu, C.-F. Shu, C.-H. Chien and Y.-T. Tao, J. Mater. Chem., 2004, 14, 1585–1589.

F. Zhang, C. Li and C. Qi, RSC Adv., 2016, 6, 102924–102930.

H. S. P. Rao, L. N. Adigopula, and K. Ramadas, ACS Comb. Sci., 2017, 19, 279–285.

H.-B. Fu and J.-N. Yao, J. Am. Chem. Soc., 2001, 123, 1434–1439.

J. Brioche, T. Courant, L. Alcaraz, M. Stocks, M. Fuber, J. Zhu, and G. Masson, Adv. Synth. Catal., 2014, 356, 1719–1724.

J. Burschka, A. Dualeh, F. Kessler, E. Baranoff, N.-L. C.-Ha, C. Yi, M. K. Nazeeruddin, and M. Grätzel, J. Am. Chem. Soc., 2011, 133, 18042–18045.

J. Sun, J. K. Qiu, B. Jiang, W. J. Hao, C. Guo, and S. J. Tu, J. Org. Chem., 2016, 81, 3321–3328.

L. Y. Zeng, T. Liu, J. Yang, Y. Yang, C. Cai, and S. Liu, ACS Comb. Sci., 2017, 19, 437–446.

M. A. Kouzehrash and A. Rahmati, Tetrahedron, 2020, 76, 130923–130930.

M. T. Nazeri, H. Farhid, S. Javanbakht, A. Shaabani, and B. Notash, Synlett, 2020, 31, 965–971.

M. T. Nazeri, S. Javanbakht, A. Shaabani, and H. R. Khavasi, ChemistrySelect, 2019, 4, 14271–14275.

M. V. Murlykina, A. D. Morozova, I. M. Zviagin, Y. I. Sakhno, S. M. Desenko, and V. A. Chebanov, Front. Chem., 2018, 6, 527.

M. X. Liu, J. R. Li, K. Zhang and D. X. Shi, Tetrahedron, 2015, 71, 7658–7662.

P.-T. Chou and Y. Chi, Chem. Eur. J., 2007, 13, 380–395.

Preeti and K. N. Singh, Org. Biomol. Chem., 2018, 16, 9084–9116.

R. Aggarwal, G. Singh, S. Kumar, T. McCabe, and I. Rozas, ChemistrySelect, 2016, 1, 5990–5994.

R. V. Sumesh, M. Muthu, A. I. Almansour, R. S. Kumar, N. Arumugam, S. Athimoolam, E. A. J. Y. Prabha, and R. R. Kumar, ACS Comb. Sci., 2016, 18, 262–270.

S. Dandia, R. Singh, J. Joshi and S. Maheshwari, Res. Chem. Intermed., 2015, 41, 4213–4226.

S. Devi, S. Kaping and J. N. Vishwakarma, Mol. Divers., 2015, 19, 759–771.

U. M. Kauhanka and M. M. Kauhanka, Liq. Cryst., 2006, 33, 121–127.

V. Kumar, K. Kaur, G. K. Gupta, and A. K. Sharma, Eur. J. Med. Chem., 2013, 69, 735–753.

W. H. Hao, P. Zhou, F. Y. Wu, B. Jiang, S. J. Tu, and G. Li, Eur. J. Org. Chem., 2016, 1968–1971.

How to Cite

Rohit Kumar*, Jitendra Kumar Chaurasiyaa, Shachi Tiwaria. (2026). Multicomponent Synthetic Reactions involving Aminopyrazole-Based Hetrocycles. International Journal of Research & Technology, 14(S1), 472–485. Retrieved from https://ijrt.org/j/article/view/1041

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