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Letters in Organic Chemistry

Author(s): Kiana F. Sina, Asieh Yahyazadeh*, Nosrat O. Mahmoodi, Kurosh R. Moghadam, Mohammad Nikpassand and Mahdi Rasa

DOI: 10.2174/1570178616666190401183953

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Ultrasonic Assisted Synthesis of 2, 3-Dihydroquinazolin-4(1H)-ones Involving Three-Component Reaction of Isatoic Anhydride, Amines and Pyrazole Carbaldehydes Catalyzed by [γ-Fe2O3@HAp-SO3H]

Page: [24 - 30] Pages: 7

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Abstract

The combination of [γ-Fe2O3@HAp-SO3H] as a catalyst and ultrasonic effect catalyzed the synthesis of diverse derivatives of 2, 3-dihydroquinazolin-4(1H)-ones which is reported in this study. The products were synthesized via the one-pot three-component reaction of isatoic anhydride, amines and pyrazole carbaldehydes in water: EtOH catalyzed by recoverable [γ-Fe2O3@HAp-SO3H]. This paper conducted an investigation of the effect of various solvents, temperatures and catalysts on the reactions. Short reaction times, mild reaction conditions, simple work-up, the desired yields and the use of an appropriate catalyst are the advantages of this novel method. The new derivatives were validated by using FT-IR, 1HNMR, and 13CNMR. Moreover, the synthesized compounds were screened for their antimicrobial activity against bacterial strains.

Keywords: 2, 3-Dihydroquinazolinone, pyrazole carbaldehydes, ultrasonic, [γ-Fe2O3@HAp-SO3H], catalyst, one-pot threecomponent reaction.

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[1]
Khan, I.; Ibrar, A.; Abbas, N.; Saeed, A. Eur. J. Med. Chem., 2014, 76, 193-244.
[2]
Zhang, J.; Cheng, P.; Ma, Y.; Liu, J.; Miao, Z.; Ren, D.; Fan, C.; Liang, M.; Liu, L. Tetrahedron Lett., 2016, 57, 5271-5277.
[3]
Olyaei, A.; Rahbarian, F.; Sadeghpour, M. Chem. Heterocycl. Compd., 2015, 51, 899-902.
[4]
Nikpassand, M.; Zare Fekri, L.; Faraji Sina, K.; Ziafatdoost Abed, S.; Marvi, O. Russ. J. Gen. Chem., 2015, 85, 1959-1964.
[5]
Kheirkhah, L.; Mamaghani, M.; Yahyazadeh, A.; Mahmoodi, N.O.A. ppl. Organomet. Chem., 2017, 32e4072
[6]
Wang, M.; Zhang, T.T.; Gao, J.J.; Liang, Y. Chem. Heterocycl. Compd., 2012, 48, 965-971.
[7]
Wang, M.; Zhang, T.T.; Liang, Y.; Gao, J.J. Chin. Chem. Lett., 2011, 22, 1423-1426.
[8]
Chen, B.; Li, J.T.; Chen, G.F. Ultrason. Sonochem., 2015, 23, 59-65.
[9]
Yang, L.J.; Luo, J.G.; Wang, X.C. Heterocycles, 2017, 94, 1027-1039.
[10]
Ghashang, M.; Azizi, K.; Moulavi Pordanjani, H. Chin. J. Chem., 2011, 29, 1617-1623.
[11]
Sharmila Rani, C.; Suresh, N.; Basaveswara Rao, M.V.; Pal, M. Arab. J. Chem., 2016, 26, 355-364.
[12]
Safari, J.; Gandomi Ravandi, S. J. Mol. Struct., 2014, 1072, 173-178.
[13]
Mamani, L.; Sheykhan, M.; Heydari, A.; Faraji, M.; Yamini, Y. Appl. Catal. A Gen., 2010, 377, 64-69.
[14]
Zhang, Z.H.; Lu, H.Y.; Yang, S.H.; Gao, J.W. J. Comb. Chem., 2010, 12, 643-646.
[15]
Zeng, L.Y.; Cai, C. J. Heterocycl. Chem., 2010, 47, 1035-1039.
[16]
Niknam, K.; Jafarpour, N.; Niknam, E. Chin. Chem. Lett., 2010, 22, 69-72.
[17]
Ma, Y.; Ren, D.; Zhang, J.; Liu, J.; Zhao, J.; Wang, L.; Zhang, F. Tetrahedron Lett., 2015, 56, 4076-4079.
[18]
Mishra, A.D. Nepal. J. Sci. Technol., 2011, 12, 133-138.
[19]
Safari, J.; Gandomi Ravandi, S. J. Saudi Chem. Soc., 2017, 21, S415-S424.
[20]
Kumar, A.; Jain, S.; Parle, M.; Jain, N.; Kumar, P. EXCLI J., 2013, 12, 1030-1042.
[21]
Almahy Dafalla, H.A. Chem. Sci. Rev. Lett., 2014, 3, 1091-1096.
[22]
Vijesh, A.M.; Isloor, A.M.; Telkar, S.; Peethambar, S.K.; Rai, S.; Isloor, N. Eur. J. Med. Chem., 2011, 45, 5591-5597.