Preety Saini , Shalu Thakur , Ankita Garg , S. S. Bari , Aman Bhalla
{"title":"立体选择性合成C-3硫代/硒基富基序修饰的反式苯并[d]恶唑基)苯基取代的β-内酰胺:各种杂环的合成中间体","authors":"Preety Saini , Shalu Thakur , Ankita Garg , S. S. Bari , Aman Bhalla","doi":"10.1080/17415993.2023.2206968","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, we reported an effectual protocol for the stereoselective synthesis of novel C-3 thio/seleno substituted <em>ortho</em>-, <em>meta</em>- and <em>para</em>-(2-benzo[<em>d</em>]oxazolyl)phenyl-β-lactams <strong>7a-i</strong>. The reaction was performed by utilizing different S/Se-alkyl/aryl substituted acids <strong>6a-d</strong> and isomeric <em>ortho</em>-, <em>meta</em>- and <em>para</em>-(2-benzo[<em>d</em>]oxazolyl)phenyl Schiff’s bases <strong>3a-c</strong> and afforded exclusive formation of <em>trans</em>-β-lactams. The <em>trans</em> configuration was assigned with respect to coupling constant values of C<em>3</em>-H and C<em>4</em>-H (<em>J</em> = 1.4 to 2.6; C3-<em>H</em> and C4-<em>H</em>). The structure elucidation of all the thio/seleno anchored β-lactams <strong>7a-i</strong> was performed using various spectroscopic techniques viz. FT-IR, NMR (<sup>1</sup>H, <sup>13</sup>C, and <sup>13</sup>C DEPT–135), 2D-NMR (<sup>1</sup>H–<sup>1</sup>H COSY and <sup>1</sup>H–<sup>13</sup>C HSQC), elemental analysis (CHN), and mass spectrometry (ESI-MS). Further, divergent substrate scope accompanied by plausible mechanistic investigation have been also described. Stereoselectivity, good functional group tolerance and excellent yield along with wider synthetic utility bestows advantages to the present protocol.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 5","pages":"Pages 602-617"},"PeriodicalIF":2.1000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Stereoselective synthesis of trans-benzo[d]oxazolyl)phenyl substituted β-lactams decorated with C-3 thio/seleno rich motifs: synthetic intermediates for diverse heterocycles\",\"authors\":\"Preety Saini , Shalu Thakur , Ankita Garg , S. S. Bari , Aman Bhalla\",\"doi\":\"10.1080/17415993.2023.2206968\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Herein, we reported an effectual protocol for the stereoselective synthesis of novel C-3 thio/seleno substituted <em>ortho</em>-, <em>meta</em>- and <em>para</em>-(2-benzo[<em>d</em>]oxazolyl)phenyl-β-lactams <strong>7a-i</strong>. The reaction was performed by utilizing different S/Se-alkyl/aryl substituted acids <strong>6a-d</strong> and isomeric <em>ortho</em>-, <em>meta</em>- and <em>para</em>-(2-benzo[<em>d</em>]oxazolyl)phenyl Schiff’s bases <strong>3a-c</strong> and afforded exclusive formation of <em>trans</em>-β-lactams. The <em>trans</em> configuration was assigned with respect to coupling constant values of C<em>3</em>-H and C<em>4</em>-H (<em>J</em> = 1.4 to 2.6; C3-<em>H</em> and C4-<em>H</em>). The structure elucidation of all the thio/seleno anchored β-lactams <strong>7a-i</strong> was performed using various spectroscopic techniques viz. FT-IR, NMR (<sup>1</sup>H, <sup>13</sup>C, and <sup>13</sup>C DEPT–135), 2D-NMR (<sup>1</sup>H–<sup>1</sup>H COSY and <sup>1</sup>H–<sup>13</sup>C HSQC), elemental analysis (CHN), and mass spectrometry (ESI-MS). Further, divergent substrate scope accompanied by plausible mechanistic investigation have been also described. Stereoselectivity, good functional group tolerance and excellent yield along with wider synthetic utility bestows advantages to the present protocol.</p></div>\",\"PeriodicalId\":17081,\"journal\":{\"name\":\"Journal of Sulfur Chemistry\",\"volume\":\"44 5\",\"pages\":\"Pages 602-617\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Sulfur Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1741599323000028\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599323000028","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Stereoselective synthesis of trans-benzo[d]oxazolyl)phenyl substituted β-lactams decorated with C-3 thio/seleno rich motifs: synthetic intermediates for diverse heterocycles
Herein, we reported an effectual protocol for the stereoselective synthesis of novel C-3 thio/seleno substituted ortho-, meta- and para-(2-benzo[d]oxazolyl)phenyl-β-lactams 7a-i. The reaction was performed by utilizing different S/Se-alkyl/aryl substituted acids 6a-d and isomeric ortho-, meta- and para-(2-benzo[d]oxazolyl)phenyl Schiff’s bases 3a-c and afforded exclusive formation of trans-β-lactams. The trans configuration was assigned with respect to coupling constant values of C3-H and C4-H (J = 1.4 to 2.6; C3-H and C4-H). The structure elucidation of all the thio/seleno anchored β-lactams 7a-i was performed using various spectroscopic techniques viz. FT-IR, NMR (1H, 13C, and 13C DEPT–135), 2D-NMR (1H–1H COSY and 1H–13C HSQC), elemental analysis (CHN), and mass spectrometry (ESI-MS). Further, divergent substrate scope accompanied by plausible mechanistic investigation have been also described. Stereoselectivity, good functional group tolerance and excellent yield along with wider synthetic utility bestows advantages to the present protocol.
期刊介绍:
The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science.
Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.