Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

One-pot of Three-component Synthesis of Novel Biologically Important 5-Amino-1,3-diaryl-1H-pyrazole-4-carbonitriles Using L-Proline Catalyst and their Antimicrobial Activity

Author(s): Mohammad Reza Poor Heravi*, Mahdis Danafar and Niloofar Poor Heravi

Volume 16, Issue 11, 2019

Page: [922 - 930] Pages: 9

DOI: 10.2174/1570178616666190315155330

Price: $65

Abstract

An expeditious three-component synthesis of various biologically important heterocyclic compounds 5-amino-1,3-diaryl-1H-pyrazole-4-carbonitriles by condensation of aryl aldehydes, malononitrile and phenylhydrazine derivatives is described. This greener protocol was catalyzed by L-Proline and proceeded efficiently in solvent at room temperature within 2-15 min.

Keywords: Multicomponent reactions, 1H-pyrazole-4-carbonitriles, L-proline, antimicrobial activity, one-pot of threecomponent, organocatalyst.

« Previous
Graphical Abstract
[1]
Bienayme, H.; Hulme, C.; Oddon, G.; Schmidtt, P. Chem. Eur. J., 2000, 6(18), 3321-3329.
[2]
Head-Gordon, T.; Hura, G. Chem. Rev., 2002, 102, 2651-2570.
[3]
Jin, T-S.; Jin, T-S.; Wang, A-Q.; Shi, F.; Han, L-S.; Liu, L-B.; Li, T-S. Arkivoc, 2006, 78-86.
[4]
(a) Khurana, J.M.; Kumar, S. Tetrahedron Lett., 2009, 50, 4125-4127.
(b) Kumar, A.; Maurya, R.A. Tetrahedron, 2007, 63, 1946-1952.
(c) Radi, M.; Bernardo, V. Bechi, B.; Castagnolo, D.; Pagano, M.; Botta, M. Tetrahedron Lett., 2009, 50, 6572-6575.
[5]
(a) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jørgensen, K.A. J. Am. Chem. Soc., 2002, 124, 827-833.
(b) Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T.C.; Kjærsgaard, A.; Jørgensen, K.A. J. Am. Chem. Soc., 2005, 127, 18296-18304.
[6]
(a) Kumar, A.; Maurya, R.A. Tetrahedron Lett., 2007, 48, 4569-4571.
(b) Bose, D.S.; Fatima, L.; Mereyala, H.B. J. Org. Chem.,2003, 68, 587-590; (b) Notz, W.; Tanaka, F.; Barbas, C.F. III. Acc. Chem. Res., 2004, 37, 580-591.
[7]
(a) Kaim, L.E.L.; Grimaud, L.; Oble, J. Angew. Chem., 2005, 117, 6101-6103.
(b) Liu, J.; Yang, Z.; Wang, Z.; Wang, F.; Chen, X.; Liu, X.; Feng, X.; Su, Z.; Hu, C. J. Am. Chem. Soc., 2008, 130, 5654-5655.
[8]
(a) Kumar, A.; Maurya, R.A. Tetrahedron Lett., 2007, 48, 4569-4571.
(b) Bose, D.S.; Fatima, L.; Mereyala, H.B. J. Org. Chem., 2003, 68, 587-590; (b) Masson, G.; Housseman, C.; Zhu, J. Angew. Chem. Int. Ed., 2007, 46, 4614-4628.
[9]
(a) Wang, L.M.; Shao, J.H.; Tian, H.; Wang, Y.H.; Liu, B. J. Fluorine. Chem., 2006, 127, 97-100.
(b) Basavaiah, D.; Rao, K.V.; Reddy, R. J. Chem. Soc. Rev., 2007, 36, 1581-1588.
[10]
(a) Hekmatshoar, R.; Majedi, S.; Bakhtiari, K. Catal. Commun., 2008, 9, 307-310.
(b) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem. Int. Ed., 2003, 42, 3677-3680.
(c) Liu, T-Y.; Cui, H-L.; Long, J.; Li, B-J.; Wu, Y.; Ding, L-S.; Chen, Y-C. J. Am. Chem. Soc., 2007, 129, 1878-1879.
[11]
(a) Seifi, M.; Sheibani, H. Catal. Lett., 2008, 126, 275-279.
(b) Rodriguez, B.; Bolm, C. J. Org. Chem., 2006, 71, 2888-2889.
[12]
(a) Kumar, A.; Maurya, R.A. Synlett, 2008, 883-885.
(b) Kumar, A.; Maurya, R.A. Tetrahedron, 2007, 63, 1946-1952.
[13]
(a) Heravi, M.M.; Jani, B.A.; Derikvand, F.; Bamoharram, F.F.; Oskooie, H.A. Catal. Commun., 2008, 10, 272-275.
(b) Hayashi, Y.; Gotoh, H.; Tamura, T.; Yamaguchi, H.; Masui, R.; Shoji, M. J. Am. Chem. Soc., 2005, 127, 16028-16029.
[14]
(a) Ziarani, G.M.; Faramarzi, S.; Asadi, S.; Badiei, A.; Bazl, R.; Amanlou, M. Iran. J. Chem. Chem. Eng., 2011, 30, 59-65.
(b) Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc., 2007, 129, 10886-10894.
[15]
(a) Herrera, R.P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem. Int. Ed., 2005, 44, 6576-6579.
(b) Gokhan-Kelekci, N.; Yabanoglu, S.; Kupeli, E.; Salgin, U.; Ozgen, O.; Ucar, G.; Yesilada, E.; Kendi, E.; Yesilada, A.; Bilgin, A.A. Bioorg. Med. Chem., 2007, 15, 5775-5786.
[16]
(a) Balalaie, S.; Bararjanian, M.; Sheikh-Ahmadi, M.; Hekmat, S.; Salehi, P. Synthetic. Commun., 2007, 37, 1097-1108.
(b) Abdolmohammadi, S.; Balalaie, S. Tetrahedron Lett., 2007, 48, 3299-3303; (b) Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc., 2006, 128, 8412-8413.
[17]
Hasaninejad, A.; Shekouhy, M.; Golzar, N. AbdolkarimZare, M.; Doroodmand, M.M. Appl. Cata. A: Gen.,2011, 402, 11-22; (b) Imada, Y.; Iida, H.; Ono, S.; Murahashi, S.-I. J. Am. Chem. Soc., 2003, 125, 2868-2869.
[18]
(a) Khurana, J.M.; Nand, B.; Saluja, P. Tetrahedron, 2010, 66, 5637-5641.
(b) Kazmaier, U. Angew. Chem. Int. Ed., 2005, 44, 2186-2188.
[19]
(a) Das, P.; Dutta, A.; Bhaumik, A.; Mukhopadhyay, C. Green Chem., 2014, 16, 1426-1435.
(b) Enders, D.; Grondal, C.; Matthias, R.M. Angew. Chem. Int. Ed., 2007, 46, 1570-1581.
[20]
(a) Khafagy, M.M.; El-Wahab, A.H.F.A.; Eid, F.A.; El-Agrody, A.M. II Farmaco, 2002, 57, 715-722.
(b) McCooey, S.H.; Connon, S. J. Angew. Chem. Int. Ed., 2005, 44, 6367-6370.
[21]
(a) Kumar, R.R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett., 2007, 17, 6459-6462.
(b) Clarke, M.L.; Fuentes, J.A. Angew. Chem. Int. Ed., 2007, 46, 930-933.
[22]
(a) Kidwai, M.; Poddar, R.; Bhardwaj, S.; Singh, S.; Luthra, P.M. Eur. J. Med. Chem., 2010, 45, 5031-5038.
(b) Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev., 2011, 111, 6984-7034.
(c) Ansari, A.; Ali, A.; Asif, M. New J. Chem., 2017, 41, 16-41.
[23]
Smith, P.W.; Sollis, S.L.; Howes, P.D.; Cherry, C.P.; Starkey, I.D.; Cobley, K.N.; Weston, H.; Scicinski, J.; Merritt, A.; Whittington, A.; Wyatt, P.; Taylor, N.; Green, D.; Bethel, R.; Madar, S.; Fenton, R.J.; Morley, P.J.; Pateman, T.; Beresford, A. Med. Chem., 1998, 41, 787-797.
[24]
Gravotto, G.; Cintas, P. Chem. Soc. Rev., 2006, 35, 180-196.
[25]
Heravi, M.R.P. Ultrason. Sonochem., 2009, 16, 361-386.
[26]
Muravyova, E.A.; Desenko, S.M.; Musatov, V.I. J. Comb. Chem., 2007, 9, 797-803.
[27]
Ratnikov, M.O.; Tumanov, V.V.; Smit, W.A. Angew. Chem. Int. Ed., 2008, 47, 9739-0742.
[28]
Selwood, D.V.; Carter, K.; Young, R.J.; Jandu, K.S. Bioorg. Med. Chem. Lett., 1996, 8, 991-994.
[29]
Singh, P.; Katyal, A.; Kalra, R.; Chandra, R. Tetrahedron Lett., 2008, 49, 727-730.
[30]
Yuasa, H.; Kajimoto, T.; Wong, C.H. Tetrahedron Lett., 1994, 35, 8243-8246.
[31]
Shelke, R.N.; Pasare, D.N.; Pawar, C.D.; Shinde, D.B.; Thore, S.N.; Pawar, R.P.; Bembalkar, S.R. Res. Rev. J. Chem., 2016, 5,2, 29-36.
[32]
National Committee for Clinical Laboratory Standards (NCCLS). Standard methods for dilution antimicrobial susceptibility tests for bacteria, which grows aerobically; National Committee on Clinical Laboratory Standards Villanova, 1982, p. 242.
[33]
Margrey Linday, E. Practical Introduction to Microbiology; (E and FN Spon. Ltd): UK, (1962), p. 177.

Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy