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

IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Sulfur Chemistry Pub Date : 2023-01-01 DOI:10.1080/17415993.2023.2206968
Preety Saini , Shalu Thakur , Ankita Garg , S. S. Bari , Aman Bhalla
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引用次数: 0

摘要

在此,我们报道了一种立体选择性合成新型C-3-硫代/硒代邻、间-和对-(2-苯并[d]恶唑基)苯基-β-内酰胺7a-i的有效方案。利用不同的S/Se烷基/芳基取代酸6a-d和同分异构体邻位、间位和对位(2-苯并[d]恶唑基)苯基席夫碱3a-c进行反应,得到反式-β-内酰胺的独家形成。反式构型是关于C3-H和C4-H的耦合常数值分配的(J=1.4至2.6;C3-H与C4-H)。使用各种光谱技术,即FT-IR、NMR(1H、13C和13C DEPT–135)、2D-NMR(1H–1H COSY和1H–13C HSQC)、元素分析(CHN)和质谱(ESI-MS),对所有硫/硒锚定的β-内酰胺7a-i的结构进行了阐明。此外,还描述了伴随着合理的机制研究的不同基质范围。立体选择性、良好的官能团耐受性和优异的产率以及更广泛的合成用途赋予了本方案优势。图形摘要
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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.

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来源期刊
Journal of Sulfur Chemistry
Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.10
自引率
9.10%
发文量
38
审稿时长
6-12 weeks
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.
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