{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T21:36:07Z","timestamp":1761514567094,"version":"3.40.5"},"reference-count":30,"publisher":"Bentham Science Publishers Ltd.","issue":"5","content-domain":{"domain":["eurekaselect.com"],"crossmark-restriction":true},"short-container-title":["COS"],"published-print":{"date-parts":[[2020,7,27]]},"abstract":"<jats:sec>\n<jats:title>Background:<\/jats:title>\n<jats:p> Reaction of \u03b1,\u03b2-unsaturated ketones with o-phenylenediamine afforded corresponding\n2,3-dihydro-1H-1,5-benzodiazepines.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Objective:<\/jats:title>\n<jats:p>\u03b1,\u03b2-Unsaturated ketones of 6-acetyl-5-hydroxy-4-methylcoumarin are precursors for synthesis of\n2,3-dihydro-1H-1,5-benzodiazepines by a reaction with o-phenylenediamine.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Methods:<\/jats:title>\n<jats:p>Enones of 6-acetyl-5-hydroxy-4-methylcoumarin were prepared from this ketone and (un)substituted\nbenzaldehydes in the presence of piperidine, triethylamine, or pyridine as a catalyst in absolute ethanol with\n1:1 molar ratios, respectively. 2',3'-Dihydro-1H-1',5'-benzodiazepines were synthesized by using the reaction\nof these enones with o-phenylenediamine in absolute ethanol in the presence of glacial acetic acid as a catalyst.\nTheir biological activities were evaluated using the disk diffusion method.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Results:<\/jats:title>\n<jats:p>Seven new 2',3'-dihydro-1H-1',5'-benzodiazepines were obtained and their structures were confirmed\nby thin-layer chromatography, IR, NMR and MS spectra. Some synthesized benzodiazepines showed antibacterial\nand antifungal activities against Escherichia coli (Gram-(\u2212) bacterium), Staphylococus epidermidis\n(Gram-(+) bacterium). Candida albicans (fungus).<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Conclusion:<\/jats:title>\n<jats:p>The formation of enones from 6-acetyl-5-hydroxy-4-methylcoumarin and (un)substituted benzaldehydes\ncould be catalyzed by piperidine, triethylamine, pyridine to afford similar yields. 2',3'-dihydro-1H-\n1',5'-benzodiazepines have been synthesized from the aforementioned enones and o-phenylenediamine.<\/jats:p>\n<\/jats:sec>","DOI":"10.2174\/1570179417666200415152105","type":"journal-article","created":{"date-parts":[[2020,4,15]],"date-time":"2020-04-15T17:51:06Z","timestamp":1586973066000},"page":"404-410","update-policy":"https:\/\/doi.org\/10.2174\/bsp_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis of some 1H-1,5-benzodiazepine Series Containing Chromene Ring from \u03b1,\u03b2-Unsaturated Ketones of 6-Acetyl-5-Hydroxy-4-Methylcoumarin"],"prefix":"10.2174","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2907-206X","authenticated-orcid":true,"given":"Duong Ngoc","family":"Toan","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Thai Nguyen University of Education, 20 Luong Ngoc Quyen, Thai Nguyen, Vietnam"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2267-1775","authenticated-orcid":true,"given":"Nguyen Dinh","family":"Thanh","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mai Xuan","family":"Truong","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Thai Nguyen University of Education, 20 Luong Ngoc Quyen, Thai Nguyen, Vietnam"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nguyen Minh","family":"Thao","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"965","reference":[{"key":"ref=1","doi-asserted-by":"publisher","first-page":"781","DOI":"10.1016\/j.molstruc.2016.07.047","volume":"1125","author":"Ahumada G.","year":"2016","unstructured":"Ahumada G.; Carrillo D.; Manzur C.; Fuentealba M.; Roisnel T.; Hamon J-R.; A facile access to new diazepines derivatives: Spectral characterization and crystal structures of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1H-1,4-diazepine and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine. 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