Iron sulfide clusters for annulation of 2-nitrobenzonitriles and benzylamines toward synthesis of 2-aryl-4-quinazolinones
DOI:
https://doi.org/10.51316/jca.2022.042Keywords:
iron(III) catalyst, condensation, N-heterocycles, annulationAbstract
A method for coupling of benzylamines and 2-nitrobenzonitriles is herein reported. Reactions proceeded in the presence of FeCl3, elemental sulfur, urea, DABCO (1,4-diazabicyclo[2.2.2]octane) base, and DMF solvent. The conditions were compatible with both electron-donating and electron-withdrawing substituents. This tactic appears to be the first method to use a first-row transition metal to promote the synthesis of 2-aryl-4-quinazolinones from commercially available 2-nitrobenzonitriles.
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E. I. Stiefel, G. N. George, in: Bioinorganic Chemistry, University Science Books, 1994, p. 365-455.
T. Herskovitz, B. A. Averill, R. H. Holm, James A. Ibers, W. D. Phillips, J. F. Weiher, Proc. Natl. Acad. Sci. U.S.A. 69 (1972) 2437-2441. https://doi.org/ 10.1073/pnas.69.9.2437
T. B. Nguyen, L. Ermolenko, A. Al-Mourabit, J. Am. Chem. Soc. 135 (2013) 118-121. https://doi.org/10.1021/ja311780a
T. B. Nguyen, P. Retailleau, A. Al-Mourabit, Org. Lett. 15 (2013) 5238-5241. https://doi.org/10.1021/ol402435c
H. Gan, Asian J. Org. Chem. 5 (2016) 1111-1114. https://doi.org/10.1002/ajoc.201600274
Q. Xing, Y. Ma, H. Xie, F. Xiao, F. Zhang, G.-J. Deng, J. Org. Chem. 84 (2019) 1238-1246. https://doi.org/10.2021/acs.joc.8b02619
T. A. To, C. T. Nguyen, M. H. P. Tran, T. Q. Huynh, T. T. Nguyen, N. T. H. Le, A. D. Nguyen, P. D. Tran, N. T. S. Phan, J. Catal. 377 (2019) 163-173. https://doi.org/10.1016/j.jcat.2019.07.008
K. X. Nguyen, P. H. Pham, A. C. D. Nguyen, C. T. Nguyen, P. D. Tran, N. T. S. Phan, J. Ind. Eng. Chem. 92 (2020) 96-100. https://doi.org/10.1016/j.jiec.2020.08.027
J. Zhou, J. Fang, J. Org. Chem. 19 (2011) 7730-7736. https://doi.org/10.1021/jo201054k
B. C. Roy, S. A. Samim, D. Panja, S. Kundu, Catal. Sci. Technol. 9 (2019) 6002-6006. https://doi.org/ 10.1039/C9CY01094G
Q. Wang, M. Lv, J. Liu, Y. Li, Q. Xu, X. Zhang, H. Cao, ChemSusChem 12 (2019) 3043-3048. https://doi.org/ 10.1002/cssc.201900265
L. Tang, X. Zhao, G. Zou, Y. Zhou, X. Yang, Asian J. Org. Chem. 5 (2016) 335-339.
https://doi.org/ 10.1002/ajoc.201500512
K. X. Nguyen, D. K. Nguyen, P. H. Pham, H. V. Le, T. T. Nguyen, N. T. S. Phan, Synlett 31 (2020) 1112-1116. https://doi.org/10.1055/s-0040-1707113
T. B. Nguyen, J. L. Bescont, L. Ermolenko, A. Al-Mourabit, Org. Lett. 15 (2013) 6218-6221. https://doi.org/10.1021/ol403064z
T. B. Nguyen, P. Retailleau, Org. Lett. 23 (2021) 5344-5348. https://doi.org/ 10.1021/acs.orglett.1c01653
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