Synthesis of Novel Bis-pyrazoles via Electrophilic Cyclization

Author(s): Adnan Cetin*.

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 6 , 2019

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

Efficient steps towards the synthesis of novel (phenyl)(1'-aryl-1,5,5'-triphenyl[3,3'-bi-1Hpyrazol]- 4-yl)methanones 4a-e were developed. The procedure starts from 1-(4-benzoyl-1,5-diphenyl- 1H-3-pyrazolyl)-3-phenyl-2-propyn-1-one (2) which was synthesized by a palladium catalyzed crosscoupling reaction. Compound 2 reacted with various hydrazines to give (E)-(phenyl)[1,5-diphenyl-3- [3-phenyl-1-(2-arylhydrazono)-2-propyn-1-yl]-1H-4-pyrazolyl]methanones E-3a-e. The bis-pyrazole derivatives 4a-e were synthesized from electrophilic cyclization reaction of α,β-acetylenic hydrazones E-3a-e and copper(I) iodide. All synthesized compounds were characterized by FT-IR, 1H, 13C NMR and Mass spectral analyses.

Keywords: Electrophilic cyclization, heterocycle, hydrazone, pyrazole, spectroscopy, antibiotic.

[1]
Çetin, A.; Bildirici, I. J. Saudi Chem. Soc., 2018, 22, 279-296.
[2]
Cetin, A.; Korkmaz, A. Opt. Mater., 2018, 85, 79-85.
[3]
Yin, P.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. Chem. Asian J., 2017, 12, 378-384.
[4]
Khan, M.F.; Alam, M.M.; Verma, G.; Akhtar, W.; Akhter, M.; Shaquiquzzaman, M. Eur. J. Med. Chem., 2016, 120, 170-201.
[5]
Vicentini, C.B.; Romagnoli, C.; Andreotti, E.; Mares, D. J. Agric. Food Chem., 2007, 55, 10331-10338.
[6]
Ahmed, B.M.; Mezei, G. J. Org. Chem., 2018, 83, 1649-1653.
[7]
Ganguly, S.; Jacob, S.K. Mini Rev. Med. Chem., 2017, 17, 959-983.
[8]
Liu, L.; Le, Y.; Teng, M.; Zhou, Z.; Zhang, D.; Zhao, C.; Cao, J. Dyes Pigm., 2018, 151, 1-6.
[9]
Sánchez-Bayo, F.; Goulson, D.; Pennacchio, F.; Nazzi, F.; Goka, K.; Desneux, N. Environ. Int., 2016, 89-90, 7-11.
[10]
Christensen, R.; Kristensen, P.K.; Bartels, E.M.; Bliddal, H.; Astrup, A. Lancet, 2007, 370, 1706-1713.
[11]
Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; Carter, J.S.; Collins, P.W.; Docter, S.; Graneto, M.J.; Lee, L.F.; Malecha, J.W.; Miyashiro, J.M.; Rogers, R.S.; Rogier, D.J.; Yu, S.S.; Anderson, G.D.; Burton, E.G.; Cogburn, J.N.; Gregory, S.A.; Koboldt, C.M.; Perkins, W.E.; Seibert, K.; Veenhuizen, A.W.; Zhang, Y.Y.; Isakson, P.C. J. Med. Chem., 1997, 40, 1347-1365.
[12]
Terrett, N.K.; Bell, A.S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett., 1996, 6, 1819-1824.
[13]
Cluck, D.; Lewis, P.; Stayer, B.; Spivey, J.; Moorman, J. J. Health Syst. Pharm, 2015, 72, 2135-2146.
[14]
Abdel-Aziz, M.; Abuo-Rahma, G.E.A.; Hassan, A.A. Eur. J. Med. Chem., 2009, 44, 3480-3487.
[15]
Ohki, H.; Hirotani, K.; Naito, H.; Ohsuki, S.; Minami, M.; Ejima, A.; Koiso, Y.; Hashimoto, Y. Bioorg. Med. Chem. Lett., 2002, 12, 3191-3193.
[16]
Yadlapalli, R.K.; Chourasia, O.P.; Vemuri, K.; Sritharan, M.; Perali, R.S. Bioorg. Med. Chem. Lett., 2012, 22, 2708-2711.
[17]
Pérez-Fernández, R.; Goya, P.; Elguero, J. Arkivoc, 2014, ii, 233-293.
[18]
Li, K.; Mohlala, M.S.; Segapelo, T.V.; Shumbula, P.M.; Guzei, I.A.; Darkwa, J. Polyhedron, 2008, 27, 1017-1023.
[19]
Cetin, A.; Korkmaz, A.; Erdoğan, E.; Kösemen, A. Mater. Chem. Phys., 2019, 222, 37-44.
[20]
Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev., 2011, 111, 6984-7034.
[21]
Zora, M.; Kivrak, A.; Yazici, C. J. Org. Chem., 2011, 76, 6726-6742.
[22]
Liu, H-L.; Jiang, H-F.; Zhang, M.; Yao, W-J.; Zhu, Q-H.; Tang, Z. Tetrahedron Lett., 2008, 49, 3805-3809.
[23]
Cetin, A. Lett. Org. Chem., 2016, 13, 310-315.
[24]
Parvatkar, P.T.; Parameswaran, P.S.; Tilve, S.G. Chem. Eur. J., 2012, 18, 5460-5489.
[25]
Qian, J-Q.; Liu, Y-K.; Zhu, J.; Jiang, B.; Xu, Z-Y. Org. Lett., 2011, 13, 4220-4223.
[26]
Kumari, K.; Raghuvanshi, D.S.; Jouikov, V.; Singh, K.N. Tetrahedron Lett., 2012, 53, 1130-1133.
[27]
Mulakayala, N.; Kandagatla, B.; Rapolu, R.K.; Rao, P.; Mulakayala, C.; Kumar, C.S.; Iqbal, J.; Oruganti, S. Bioorg. Med. Chem. Lett., 2012, 22, 5063-5066.
[28]
Safaei, S.; Mohammadpoor-Baltork, I.; Khosropour, A.R.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V. Synlett, 2011, 2214-2222.
[29]
Bekhit, A.A.; Hymete, A.; Bekhit, A.E.A.; Damtew, A.; Aboul-Enein, H.Y. Mini Rev. Med. Chem., 2010, 10, 1014-1033.
[30]
Schmidt, A.; Dreger, A. Curr. Org. Chem., 2011, 15, 1423-1463.
[31]
Evindar, G.; Batey, R.A. J. Org. Chem., 2006, 71, 1802-1808.
[32]
Zora, M.; Kivrak, A. J. Org. Chem., 2011, 76, 9379-9390.
[33]
Akcamur, Y.; Sener, A.; Ipekoglu, A.M.; Kollenz, G. J. Heterocycl. Chem., 1997, 34, 221-224.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 16
ISSUE: 6
Year: 2019
Page: [511 - 516]
Pages: 6
DOI: 10.2174/1570178615666181106155555
Price: $65

Article Metrics

PDF: 22
HTML: 2