{"title":"6-hydroxy-4,7-dimethoxybenzofuranylcarbonyl tethered annulated pyridines 的合成和抗菌评估","authors":"Najla A. Alshaye , Magdy A. Ibrahim","doi":"10.1080/00397911.2024.2342358","DOIUrl":null,"url":null,"abstract":"<div><p>2-Chloro-5-[(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)carbonyl]pyridine-3-carbonitrile (<strong>3</strong>) was synthesized and its chemical reactivity was investigated toward a diversity of binucleophiles. Treatment of compound <strong>3</strong> hydrazine hydrate and phenylhydrazine produced pyrazolo[3,4-<em>b</em>]pyridines while isoxazolo[5,4-<em>b</em>]pyridine was obtained from reacting compound <strong>3</strong> with hydroxylamine. A diversity of pyrido[2,3-<em>d</em>]pyrimidines was synthesized from treatment of staring substrate <strong>3</strong> with some 1,3-<em>N</em>,<em>N</em>-binucleophiles. Treating compound <strong>3</strong> with some 1,4-binucleophiles including ethylenediamine, <em>o</em>-phenylenediamine, 2-aminophenol and 2-aminothiophenol furnished pyrido[2,3-<em>e</em>][1,4]diazepine <strong>12</strong> and pyrido[2,3-<em>b</em>][1,5] benzodiazepine <strong>13</strong>, pyrido[2,3-<em>b</em>][1,5]benzoxazepine <strong>14</strong> and pyrido[2,3-<em>b</em>][1,5] benzothiazepine <strong>15</strong>, respectively. The synthesize compounds shown remarkable effect against yeast and fungus, while compounds <strong>4</strong> and <strong>7</strong>–<strong>11</strong> exhibit excellent efficacy against all types of Gram + and Gram - bacteria. Structures of the produced compounds were established using analytical and spectroscopic tools.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 10","pages":"Pages 815-825"},"PeriodicalIF":1.8000,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and antimicrobial evaluation of 6-hydroxy-4,7-dimethoxybenzofuranylcarbonyl tethered annulated pyridines\",\"authors\":\"Najla A. Alshaye , Magdy A. Ibrahim\",\"doi\":\"10.1080/00397911.2024.2342358\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>2-Chloro-5-[(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)carbonyl]pyridine-3-carbonitrile (<strong>3</strong>) was synthesized and its chemical reactivity was investigated toward a diversity of binucleophiles. Treatment of compound <strong>3</strong> hydrazine hydrate and phenylhydrazine produced pyrazolo[3,4-<em>b</em>]pyridines while isoxazolo[5,4-<em>b</em>]pyridine was obtained from reacting compound <strong>3</strong> with hydroxylamine. A diversity of pyrido[2,3-<em>d</em>]pyrimidines was synthesized from treatment of staring substrate <strong>3</strong> with some 1,3-<em>N</em>,<em>N</em>-binucleophiles. Treating compound <strong>3</strong> with some 1,4-binucleophiles including ethylenediamine, <em>o</em>-phenylenediamine, 2-aminophenol and 2-aminothiophenol furnished pyrido[2,3-<em>e</em>][1,4]diazepine <strong>12</strong> and pyrido[2,3-<em>b</em>][1,5] benzodiazepine <strong>13</strong>, pyrido[2,3-<em>b</em>][1,5]benzoxazepine <strong>14</strong> and pyrido[2,3-<em>b</em>][1,5] benzothiazepine <strong>15</strong>, respectively. The synthesize compounds shown remarkable effect against yeast and fungus, while compounds <strong>4</strong> and <strong>7</strong>–<strong>11</strong> exhibit excellent efficacy against all types of Gram + and Gram - bacteria. Structures of the produced compounds were established using analytical and spectroscopic tools.</p></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":\"54 10\",\"pages\":\"Pages 815-825\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-05-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0039791124000353\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000353","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis and antimicrobial evaluation of 6-hydroxy-4,7-dimethoxybenzofuranylcarbonyl tethered annulated pyridines
2-Chloro-5-[(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)carbonyl]pyridine-3-carbonitrile (3) was synthesized and its chemical reactivity was investigated toward a diversity of binucleophiles. Treatment of compound 3 hydrazine hydrate and phenylhydrazine produced pyrazolo[3,4-b]pyridines while isoxazolo[5,4-b]pyridine was obtained from reacting compound 3 with hydroxylamine. A diversity of pyrido[2,3-d]pyrimidines was synthesized from treatment of staring substrate 3 with some 1,3-N,N-binucleophiles. Treating compound 3 with some 1,4-binucleophiles including ethylenediamine, o-phenylenediamine, 2-aminophenol and 2-aminothiophenol furnished pyrido[2,3-e][1,4]diazepine 12 and pyrido[2,3-b][1,5] benzodiazepine 13, pyrido[2,3-b][1,5]benzoxazepine 14 and pyrido[2,3-b][1,5] benzothiazepine 15, respectively. The synthesize compounds shown remarkable effect against yeast and fungus, while compounds 4 and 7–11 exhibit excellent efficacy against all types of Gram + and Gram - bacteria. Structures of the produced compounds were established using analytical and spectroscopic tools.
期刊介绍:
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.