Abstract
2, 3-Dihydroquinazolinones are of popular compounds with the diversification of biological and pharmacological activities. Among many discovered methods, there are efficient and convenient methods used for the synthesis of 2, 3-dihydroquinazoline-4 (1H)-one and some new bis 2, 3- dihydroquinazoline-4 (1H)-one derivatives which are reported in this study. The mentioned methods include the two-component condensation of one molecule of anthranilamide and one molecule of pyrazole carbaldehyde using montmorillonite-K10 as a catalyst for the preparation of 2, 3 dihydroquinazoline- 4 (1H)-ones. Also, one-pot pseudo-five-component reaction (5MCRs) of two molecules of isatoic anhydride, two molecules of pyrazole carbaldehydes and one molecule of ethan-1, 2-diamine in the presence of the r catalyst (montmorillonite-K10) for the synthesis of bis 2, 3-dihydroquinazoline-4 (1H)-ones. Despite the short times of reactions, high yields of products were obtained, which were validated using FT-IR, 1HNMR, 13CNMR, and elemental analysis. Moreover, the compounds were screened for their antimicrobial activities against two-gram-positive bacterial strains: Staphylococcus aureus and Micrococcus Luteus; and against two-gram-negative bacterial strains, as well: Escherichia coli and Pseudomonas aeruginosa, which all were utilized for antibacterial investigations. The results showed moderate or significant antibacterial activities.
Keywords: 2, 3-Dihydroquinazolinone, bis 2, 3-dihydroquinazolinone, one-pot pseudo-five-component reaction (5MCRs), pyrazole carbaldehyde, montmorillonite-K10, antibacterial activity.
Graphical Abstract
[http://dx.doi.org/10.1016/j.saa.2016.07.038] [PMID: 27494220]
[http://dx.doi.org/10.1021/acs.joc.6b02914] [PMID: 28121145]
[http://dx.doi.org/10.1080/17518253.2015.1109145]
[http://dx.doi.org/10.2174/1570178616666190401183953]
[http://dx.doi.org/10.1002/jhet.2292]
[http://dx.doi.org/10.1134/S1070363215080265]
[http://dx.doi.org/10.1016/j.tetlet.2019.05.030]
[http://dx.doi.org/10.1016/j.cdc.2019.100230]
[http://dx.doi.org/10.1186/s13065-019-0517-7] [PMID: 31355367]
[http://dx.doi.org/10.1080/00397911.2018.1506033]
[http://dx.doi.org/10.14233/ajchem.2016.19676]
[http://dx.doi.org/10.1007/s11164-016-2587-7]
[http://dx.doi.org/10.1016/j.cclet.2016.06.001]
[http://dx.doi.org/10.1016/j.tetlet.2016.09.077]
[http://dx.doi.org/10.1016/j.tetlet.2013.08.037]
[http://dx.doi.org/10.4103/1687-4315.197580]
[http://dx.doi.org/10.1002/jhet.2609]
[http://dx.doi.org/10.1007/s13738-017-1124-y]
[http://dx.doi.org/10.1007/s11164-013-1131-2]
[http://dx.doi.org/10.1007/s10593-011-0846-5]
[http://dx.doi.org/10.1155/2011/870902] [PMID: 22567248]
[PMID: 27298613]
[http://dx.doi.org/10.1039/c3nj00618b]
[http://dx.doi.org/10.1016/j.cclet.2015.07.026]
[http://dx.doi.org/10.1016/j.tetlet.2016.10.047]