Abstract
Pyrazole and its derivatives are an important class of heterocyclic compounds, present in several biologically and medicinally active compounds. Compounds containing 2,4-dihydro-3H-pyrazol-3-one structural motif, including 4,4′-(arylmethylene)-bis-(1H-pyrazol-5-ols), have attracted interest because they exhibit a wide range of biological activities and as the chelating and extracting reagents for different metal ions. There are two main strategies to the synthesis of bis(pyrazolyl)methane derivatives. The first involves the one-pot pseudo three-component reactions of 3-methyl-5-pyrazolone derivatives and aldehydes, and the second approach is the one-pot pseudo five-component reactions of β-keto esters, hydrazins and aldehydes. This review includes the recent investigation in the multi-component synthesis and their applications of bis(pyrazolyl)methanes and describes the literature reports for the period of 2014 to early 2021.
Graphic abstract
Similar content being viewed by others
References
B.N. Acharya, D. Saraswat, M. Tiwari, A.K. Shrivastava, R. Ghorpade, S. Apna, M.P. Kaushik, Eur. J. Med. Chem. 45, 430 (2010)
A. Tanitam, Y. Oyamada, K. Ofugi, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, J. Yamagishi, J. Med. Chem. 47, 3693 (2004)
P. Cali, L. Naerum, S. Mukhija, A. Hjelmencrantz, Bioorg. Med. Chem. Lett. 14, 5997 (2004)
K.H. Carlsson, I. Jurna, Naunyn-Schmiedebergs Arch. Pharmacol. 335, 154 (1987)
S. Sugiura, S. Ohno, O. Ohtani, K. Izumi, T. Kitamikado, H. Asai, K. Kato, J. Med. Chem. 20, 80 (1977)
M. Kidwai, R.J. Mohan, J. Korean Chem. Soc. 48, 177 (2004)
K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19, 4501 (2009)
C.E. Rosiere, M.I. Grossman, Science 113, 651 (1951)
D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28, 256 (1985)
M.A.I. Salem, E.A. Soliman, M.B. Smith, M.R. Mahmoud, M.E. Azab, Phosphorus Sulfur Silicon Relat. Elem. 179, 61 (2004)
R.V. Antre, A. Cendilkumar, R. Nagarajan, D. Goli, R.J. Oswal, J. Sci. Res. 4, 183 (2012)
Y. Xiaohui, Z. Pinghu, Z. Yonghong, W. Junsong, L. Hongjun, Chin. J. Chem. 30, 670 (2012)
R.N. Mahajan, F.H. Havaldar, P.S. Fernandes, J. Indian Chem. Soc. 68, 245 (1991)
P.M.S. Chauhan, S. Singh, R.K. Chatterjee, Indian J. Chem. Sect. B 32, 858 (1993)
G. Mariappan, P.B. Saha, L. Sutharson, A. Haldar, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 49, 1671 (2010)
D. Singh, D. Singh, J. Indian Chem. Soc. 68, 165 (1991)
M. Londershausen, Pestic. Sci. 48, 269 (1996)
A.B. Uzoukwu, Polyhedron 12, 2719 (1993)
D.H. Jani, H.S. Patel, H. Keharia, C.K. Modi, Appl. Organometal. Chem. 24, 99 (2010)
A.D. Garnovskii, A.I. Uraev, V.I. Minkin, Arkivoc iii, 29 (2004)
D. Slngh, D. Slngh, J. Chem. Eng. Data 29, 355 (1984)
L. Henning, M. Alva-Astudillo, G. Mann, T. Kappe, Monatsh. Chem. 123, 571 (1992)
X.-L. Li, Y.-M. Wang, B. Tian, T. Matsuura, J.-B. Meng, J. Heterocycl. Chem. 35, 129 (1998)
F. Risitano, G. Grassi, F. Foti, C. Bilardo, Tetrahedron 56, 9669 (2000)
N.H.S. Ammida, A. Giath, Asian J. Chem. 15, 616 (2003)
W. Wang, S.-X. Wang, X.-Y. Qin, J.-T. Li, Synth. Commun. 35, 1263 (2005)
C.-S. Yao, C.-X. Yu, S.-J. Tu, D.-Q. Shi, X.-S. Wang, Y.-Q. Zhu, H.-Z. Yang, J. Fluor. Chem. 128, 105 (2007)
M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Synthesis 12, 1933 (2008)
C. Guo, W. Holzer, Molbank. 2009, M605 (2009)
K. Niknam, D. Saberi, M. Sadegheyan, A. Deris, Tetrahedron Lett. 51, 692 (2010)
E. Mosaddegh, A. Hhassankhani, A. Baghizadeh, J. Chil. Chem. Soc. 55, 41 (2010)
A.A. Al-Mutairi, F.E.M. El-Baih, H.M. Al-Hazimi, J. Saudi Chem. Soc. 14, 287 (2010)
C. Yang, L. Pang, A. Wang, Asian J. Chem. 23, 749 (2011)
A. Hasaninejad, M. Shekouhy, A. Zare, S.M.S.H. Ghattali, N. Golzar, J. Iran. Chem. Soc. 8, 411 (2011)
S. Tayebi, M. Baghernejad, D. Saberi, K. Niknam, Chin. J. Catal. 32, 1477 (2011)
N.P. Tale, G.B. Tiwari, N.N. Karade, Chin. Chem. Lett. 22, 1415 (2011)
K. Niknam, S. Mirzaee, Synth. Commun. 41, 2403 (2011)
A. Hasaninejad, A. Zare, M. Shekouhy, N. Golzar, Org. Prep. Proced. Int. 43, 131 (2011)
H. Zang, Q. Su, Y. Mo, B. Cheng, Ultrason. Sonochem. 18, 68 (2011)
M. Baghernejad, K. Niknam, Int. J. Chem. 4, 52 (2012)
S. Sobhani, A.-R. Hasaninejad, M.F. Maleki, Z.P. Parizi, Synth. Commun. 42, 2245 (2012)
Z. Karimi-Jaberi, B. Pooladian, M. Moradi, E. Ghasemi, Chin. J. Catal. 33, 1945 (2012)
A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, Z. Asgari, M. Shekouhy, A. Zare, A. Hasaninejad, RSC Adv. 2, 8010 (2012)
M.A. Gouda, A.A. Abu-Hashem, Green Chem. Lett. Rev. 5, 203 (2012)
B.S. Kuarm, B. Rajitha, Synth. Commun. 42, 2382 (2012)
K.R. Phatangare, V.S. Padalkar, V.D. Gupta, V.S. Patil, P.G. Umape, N. Sekar, Synth. Commun. 42, 1349 (2012)
S. Sobhani, R. Nasseri, M. Honarmand, Can. J. Chem. 90, 798 (2012)
S. Bhavanarushi, V. Kanakaiah, G. Bharath, A. Gangagnirao, J.V. Rani, Med. Chem. Res. 23, 158 (2014)
K. Niknam, M. Sadeghi Habibabad, A. Deris, N. Aeinjamshid, Monatsh. Chem. 144, 987 (2013)
N. Iravani, J. Albadi, H. Momtazan, M. Baghernejad, J. Chin. Chem. Soc. 60, 418 (2013)
A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A: Gen. 467, 61 (2013)
K.P. Broujeni, P. Shojaei, Turk. J. Chem. 37, 756 (2013)
S. Sobhani, E. Safaei, A.-R. Hasaninejad, S. Rezazadeh, J. Organomet. Chem. 694, 3027 (2009)
S. Tayebi, K. Niknam, Iran. J. Catal. 2, 69 (2012)
J. Xu-dong, D. Hai-feng, L. Ying-jie, C. Jun-gang, L. Da-peng, W. Mao-cheng, Chem. Res. Chin. Univ. 28, 999 (2012)
E. Soleimani, S. Ghorbani, M. Taran, A. Sarvary, C. R. Chimie 15, 955 (2012)
X.-C. Tu, H. Feng, M.-S. Tu, B. Jiang, S.-L. Wang, S.-J. Tu, Tetrahedron Lett. 53, 3169 (2012)
M. Seddighi, F. Shirini, M. Mamaghani, RSC Adv. 3, 24046 (2013)
A. Hasaninejed, M.R. Kazerooni, A. Zare, ACS Sustain. Chem. Eng. 1, 679 (2013)
M.A. Gouda, J. Heterocycl. Chem. 53, 356 (2016)
B. Sadeghi, M.G. Rad, Iran. J. Catal. 4, 67 (2014)
K. Eskandari, B. Karami, S. Khodabakhshi, Chem. Heterocycl. Compd. 50, 1658 (2015)
A. Zare, M. Merajoddin, A.R. Moosavi-Zare, M. Zarei, Chin. J. Catal. 35, 85 (2014)
A.D. Gupta, R. Pal, A.K. Mallik, Green Chem. Lett. Rev. 7, 404 (2014)
M. Barge, R. Salunkhe, RSC Adv. 4, 31177 (2014)
K. Eskandari, B. Karami, S. Khodabakhshi, M. Farahi, Lett. Org. Chem. 12, 38 (2015)
M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, RSC Adv. 5, 71942 (2015)
K.M. Khan, M.T. Muhammad, I. Khan, S. Perveen, W. Voelter, Monatsh. Chem. 146, 1587 (2015)
A. Vafaee, A. Davoodnia, M. Pordel, Res. Chem. Intermed. 41, 8343 (2015)
A. Zare, F. Abi, V. Khakyzadeh, A.R. Moosavi-Zare, A. Hasaninejad, M. Zarei, Iran. J. Catal. 5, 311 (2015)
M.N. Elinson, O.O. Sokolova, R.F. Nasybullin, Heterocycl. Commun. 21, 97 (2015)
B. Sadeghi, M.G. Rad, Synth. React. Inorg. M. 45, 1723 (2015)
K. Eskandari, B. Karami, S. Khodabakhshi, S.J. Hoseini, Turk. J. Chem. 39, 1069 (2015)
S. Sobhani, S. Asadi, M. Salimi, F. Zarifi, J. Organomet. Chem. 822, 154 (2016)
M. Safaiee, M.A. Zolfigol, F. Derakhshan-Panah, V. Khakyzadeh, L. Mohammadi, Croat. Chem. Acta 89, 317 (2016)
S.S. Kauthale, S.U. Tekale, K.M. Jadhav, R.P. Pawar, Mol. Divers. 20, 763 (2016)
M.A. Zolfigol, A. Khazaei, F. Karimitabar, M. Hamidi, Appl. Sci. 6, 27 (2016)
M. Keshavarz, M. Vafaei-Nezhad, Catal. Lett. 146, 353 (2016)
X. Gu, Z. Fang, J. Chem. Res. 40, 683 (2016)
E. Mosaddegh, M.R. Islami, Z. Shojaie, Arab. J. Chem. 10, S1200 (2017)
H. Banari, H. Kiyani, A. Pourali, Res. Chem. Intermed. 43, 1635 (2017)
S.J. Saghanezhad, M.H. Sayahi, I. Imanifar, M. Mombeni, S.D. Hamood, Res. Chem. Intermed. 43, 6521 (2017)
A. Zare, E. Sharif, A. Arghoon, M. Ghasemi, B. Dehghani, S. Ahmad-Zadeh, F. Zarei, Iran. J. Catal. 7, 233 (2017)
M.A. Zolfigol, M. Navazeni, M. Yarie, R. Ayazi-Nasrabadi, Appl. Organometal. Chem. 31, e3633 (2017)
M. Bakherad, A. Keivanloo, A.H. Amin, R. Doosti, Z. Aghayan, J. Appl. Chem. 11, 31 (2017)
S.N.A.B.D. Elal, A.O. Al-Dossary, ejpmr 4, 685 (2017)
Q. ul-ain, S. Perveen, M.T. Muhammad, S. Yousuf, K.M. Khan, M.I. Choudhary, J. Chem. Soc. Pak. 40, 563 (2018)
M. Safaiee, M.A. Zolfigol, F. Derakhshan-Panah, F. Taayoshi, J. Appl. Chem. 12, 51 (2018)
M. Keshavarz, A.Z. Ahmady, L. Vaccaro, M. Kardani, Molecules 23, 330 (2018)
S. Yousuf, K.M. Khan, U. Salar, A. Jabeen, S. Ahmed, M.T. Muhammad, A. Faheem, S. Perveen, Med. Chem. 14, 536 (2018)
H. Filian, A. Ghorbani-Choghamarani, E. Tahanpesar, J. Iran. Chem. Soc. 16, 2673 (2019)
E. Rostami, Z. Kordrostami, Asian J. Nanosci. Mater. 3, 203 (2020)
P.G. Patil, S. Sehlangia, D.H. More, Synth. Commun. 50, 1696 (2020)
M. Nikoorazm, M. Khanmoradi, M. Mohammadi, Appl. Organometal. Chem. 34, e5504 (2020)
M. Nikoorazm, M. Mohammadi, M. Khanmoradi, Appl. Organomet. Chem. 34, e5704 (2020)
K. Eskandari, B. Karami, Org. Prep. Proced. Int. 52, 192 (2021)
J.E. Cadena-Cruz, L.M. Guamán-Ortiz, J.C. Romero-Benavides, N. Bailon-Moscoso, K.E. Murillo-Sotomayor, N.V. Ortiz-Guamán, J. Heredia-Moya, BMC Chem. 15, 38 (2021)
Z. Zhou, Y. Zhang, Green Chem. Lett. Rev. 7, 18 (2014)
J. Safaei-Ghomi, B. Khojastehbakht-Koopaei, H. Shahbazi-Alavi, RSC Adv. 4, 46106 (2014)
A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, New J. Chem. 38, 5287 (2014)
A. Hassankhani, J. Mex. Chem. Soc. 59, 1 (2015)
M. Zarghani, B. Akhlaghinia, RSC Adv. 5, 87769 (2015)
J. Safaei-Ghomi, B. Khojastehbakht-Koopaei, S. Zahedi, Chem. Heterocycl. Compd. 51, 34 (2015)
F. Shirini, M. Seddighi, M. Mazloumi, M. Makhsous, M. Abedini, J. Mol. Liq. 208, 291 (2015)
Z. Zhou, Y. Zhang, J. Chil. Chem. Soc. 60, 2992 (2015)
M.A. Gouda, M.M.M. Al-Balawi, A.A. Abu-Hashem, Eur. J. Chem. 7, 363 (2016)
N.G. Khaligh, S.B. Hamid, S.J.J. Titinchi, Chin. Chem. Lett. 27, 104 (2016)
D. Zhang, Y. Zhang, T. Zhao, J. Li, Y. Hou, Q. Gu, Tetrahedron 72, 2979 (2016)
J. Safaei-Ghomi, M. Asgari-Keirabadi, B. Khojastehbakht-Koopaei, H. Shahbazi-Alavi, Res. Chem. Intermed. 42, 827 (2016)
A.R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, O. Khaledian, B. Shirmardi Shaghasemi, Res. Chem. Intermed. 42, 4759 (2016)
N.G. Khaligh, S.J.J. Titinchi, S.B.A. Hamid, H.S. Abbo, Polycycl. Aromat. Compd. 36, 716 (2016)
M. Fatahpour, F.N. Sadeh, N. Hazeri, M.T. Maghsoodlou, M.S. Hadavi, S. Mahnaei, J. Saudi Chem. Soc. 21, 998 (2017)
D. Banerjee, R. Karmakar, U. Kayal, G. Maiti, Synth. Commun. 47, 1006 (2017)
M. Fatahpour, F.N. Sadeh, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, J. Iran. Chem. Soc. 14, 1945 (2017)
P.S. Mahajan, M.D. Nikam, V. Khedkar, P. Jha, P.V. Badadhe, C.H. Gill, J. Heterocycl. Chem. 54, 1109 (2017)
S. Sobhani, F. Zarifi, J. Skibsted, ACS Sustain. Chem. Eng. 5, 4598 (2017)
R. Ramesh, N. Nagasundaram, D. Meignanasundar, P. Vadivel, A. Lalitha, Res. Chem. Intermed. 43, 1767 (2017)
R. Jahanshahi, B. Akhlaghinia, Chem. Pap. 71, 1351 (2017)
H. Shahbazi-Alavi, J. Safaei-Ghomi, S. Esmaili, S.H. Nazemzadeh, J. Chem. Res. 41, 457 (2017)
A.R. Moosavi-Zare, H. Goudarziafshar, S. Dastbaz, J. Chin. Chem. Soc. 64, 727 (2017)
C. Yang, P.-Z. Liu, D.-Z. Xu, Chemistry Select 2, 1232 (2017)
M.A. Shaikh, M. Farooqui, S. Abed, Iran. J. Catal. 8, 73 (2018)
J. Safaei-Ghomi, H. Shahbazi-Alavi, A. Ziarati, Sci. Iran. C 25, 3288 (2018)
Z. Abshirini, A. Zare, Z. Naturforsch. B 53, 191 (2018)
T. Wang, Y. Yu, X. Qing, C. Dai, C. Wang, J. Chem. Res. 42, 313 (2018)
M. Karami, A. Zare, Org. Chem. Res. 4, 174 (2018)
M. Shekouhy, R. Kordnezhadian, A. Khalafi-Nezhad, J. Iran. Chem. Soc. 15, 2357 (2018)
F. Diwan, M. Shaikh, M. Farooqui, Chem. Biol. Interface 8, 255 (2018)
F. Noruzian, A. Olyaei, R. Hajinasiri, Res. Chem. Intermed. 45, 4383 (2019)
R. Khalifeh, R. Shahimoridi, M. Rajabzadeh, Catal. Lett. 149, 2864 (2019)
J. Milani, M.T. Maghsoodlou, N. Hazeri, M. Nassiri, J. Iran. Chem. Soc. 16, 1651 (2019)
F. Noruzian, A. Olyaei, R. Hajinasiri, M. Sadeghpour, Synth. Commun. 49, 2717 (2019)
N.G. Khaligh, T. Mihankhah, H. Gorjian, M.R. Johan, Synth. Commun. 50, 3276 (2020)
N.G. Khaligh, T. Mihankhah, J. Heterocycl, Chem. 57, 4036 (2020)
A. Singh, K.R. Ansari, M.A. Quraishi, S. Kaya, J. Mol. Struct. 1206, 127685 (2020)
S.R. Kolsepatil, D. Wagare, D.L. Lingampalle, Heterocycl. Lett. 10, 309 (2020)
T. Tamoradi, S.M. Mousavi, M. Mohammadi, New J. Chem. 44, 8289 (2020)
N.G. Shabalala, N. Kerru, S. Maddila, W.E. van Zyl, S.B. Jonnalagadda, Chem. Data Coll. 28, 100467 (2020)
F. Rezaei, M.A. Amrollahi, R. Khalifeh, Chem. Sel 5, 1760 (2020)
H. Filian, A. Kohzadian, M. Mohammadi, A. Ghorbani-Choghamarani, A. Karami, Appl. Organometal. Chem. 34, e5579 (2020)
A. Kohzadian, H. Filian, Z. Kordrostami, A. Zare, A. Ghorbani-Choghamarani, Res. Chem. Intermed. 46, 1941 (2020)
A. Savari, F. Heidarizadeh, Polycycl. Aromat. Comp. 41, 1343 (2021)
H.F. Niya, N. Hazeri, M. Fatahpour, P. Roudini, M. Shirzaei, J. Mol. Struct. 1239, 130400 (2021)
R.C. Patil, S.A. Damate, D.N. Zambare, S.S. Patil, New J. Chem. 45, 9152 (2021)
Acknowledgements
The authors thank the Research Council of Islamic Azad University of Takestan and Payame Noor University for financial supports.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Sadeghpour, M., Olyaei, A. Recent advances in the synthesis of bis(pyrazolyl)methanes and their applications. Res Chem Intermed 47, 4399–4441 (2021). https://doi.org/10.1007/s11164-021-04592-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-021-04592-7