Abstract
A highly efficient and general method is applied for the multicomponent synthesis of quinazolinone derivatives from cyclocondensation of aromatic aldehydes and dimedone with 2-amino benzimidazole or 3-amino-1,2,4-triazole using nano-SiO2 as a catalyst in acetonitrile at room temperature. In this method, nano-SiO2 was used as a green and reusable catalyst. This synthetic method provides several advantages including excellent yields, short reaction times, simple workup, mild conditions and inexpensiveness, green, and recyclable.
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E.M. Gordon, R.W. Barret, W.I. Dower, S.P. Fodor, M.A. Gallop, J. Med. Chem. 37, 1385 (1994)
M.A. Gallop, R.W. Barret, W.J. Dower, S.P. Fodor, E.M. Gordon, J. Med. Chem. 37, 1233 (1994)
A. Golisade, J. Wiesner, C. Herforth, H. Joma, A. Link, Bioorg. Med. Chem. 10, 769 (2002)
C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)
A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
A. Shaabani, A. Rahmati, A.H. Rezayan, H.R. Khavasi, J. Iran. Chem. Soc. 8, 24 (2011)
A. Shaabani, A. Rahmati, A.H. Rezayan, M. Darvishi, Z. Badri, A. Sarvari, QSAR Comb. Sci. 26, 973 (2007)
A. Monge, J.A. Palop, J.C.D. Castillo, J.M. Caldero, J. Roca, G. Romero, J.D. Rio, B. Lasheras, J. Med. Chem. 36, 2745 (1993)
K. Toshima, R. Takano, T. Ozawa, S. Matsumara, Chem. Commun. 3, 212 (2002)
B. Dowlati, D. Nematollahi, M.R. Othman, Int. J. Electrochem. Sci. 7, 5990 (2012)
Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14, 541 (2004)
P.A.G.M. De Smet, Drugs 54, 801 (1997)
J.D. Garcia, R. Somanathan, I.A. Rivero, G. Aguirre, L.H. Hellberg, Synth. Commun. 30, 2707 (2000)
V.J. Ram, R.C. Srimal, D.S. Kushwaha, L. Mishra, J. Prakt. Chem. 332, 629 (1990)
V. Alagarsamy, V.R. Solomon, G. Vanikavitha, V. Paluchamy, M. Ravichandran, A. Arnaldsujin, A. Thangathirupathy, S. Amuthalakshmi, R. Revathi, Biol. Pharm. Bull. 25, 1432 (2002)
V. Alagarsamy, G. Murugananthan, R. Venkateshperumal, Biol. Pharm. Bull. 26, 1711 (2003)
V. Alagarsamy, R. Venkatesaperumal, S. Vijayakumar, T. Angayarkanni, P. Pounammal, S. Senthilganesh, S. Kandeeban, Pharmazie. 57, 306 (2002)
V. Alagarsamy, Pharmazie 59, 753 (2004)
V. Alagarsamy, V.R. Solomon, M. Murugan, Bioorg. Med. Chem. 15, 4009 (2007)
H. MannJen, H. Li Jiau, K. Sheng Chu, X. Yi Bastow, B. Kenneth, N. Y. Hamel, E. Lee, K. Hsiung, J. Med. Chem. 43, 4479 (2000)
V. Alagarsamy, R. Revathi, S. Meena, K.V. Ramaseshu, S. Rajasekaran, E. De Clercq, Indian J. Pharm. Sci. 66, 459 (2004)
K.-C. Liu, M.-K. Hu, Arch. Pharm. 319, 188 (1986)
T. Eicher, S. Hauptmann, Chemie der Heterocyclen (Georg Thieme, Stuttgart, New York, 1994), p. 398
V. Haridas, K. Lal, Y.K. Sharma, Tetrahedron Lett. 48, 4719 (2007)
V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457 (2007)
A. Shaabani, A. Rahmati, E. Farhangi, A.H. Rezayan, Monatsh. Chem. 138, 615 (2007)
M.M. Heravi, L. Ranjbar, F. Derikvand, B. Alimadadi, H.A. Oskooie, F.F. Bamoharram, Mol. Divers. 12, 181 (2008)
G. Krishnamurthy, K.V. Jagannath, J. Chem. Sci. 125, 807 (2013)
R.G. Puligoundla, S. Karnakanti, R. Bantu, N. Kommu, S.B. Kondra, L. Nagarapu, Tetrahedron Lett. 54, 2480 (2013)
V.V. Lipson, S.M. Desenko, S.V. Shishkina, M.G. Shirobokova, O.V. Shishkin, V.D. Orlov, Chem. Heterocycl. Compd. 39, 1041 (2003)
V.V. Lipson, S.M. Desenko, M.G. Shirobokova, V.V. Borodina, Chem. Heterocycl. Compd. 39, 1213 (2003)
J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, Chin. Chem. Lett. 24, 921 (2013)
J. Albadi, A. Mansournezhad, Z. Derakhshandeh, Chin. Chem. Lett. 24, 821 (2013)
F.F. Bamoharram, M.M. Heravi, H. Teymouri, M. Zebarjad, A. Ahmadpour, Synth. React. Inorg. Met.-Org. Chem. 41, 1221 (2011)
E. Rafiee, M. Khodayari, M. Kahrizi, R. Tayebee, J. Mol. Catal. A: Chem. 358, 121 (2012)
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The University of Sistan and Baluchestan is thanked for supporting this work.
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Mousavi, M.R., Maghsoodlou, M.T. Nano-SiO2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives. J IRAN CHEM SOC 12, 743–749 (2015). https://doi.org/10.1007/s13738-014-0533-4
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DOI: https://doi.org/10.1007/s13738-014-0533-4