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NHC catalyzed radical tandem cyclization: an efficient synthesis of α,α-difluoro-γ-lactam derivatives† NHC 催化的自由基串联环化：α,α-二氟-γ-内酰胺衍生物的高效合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01012d
{"title":"NHC catalyzed radical tandem cyclization: an efficient synthesis of α,α-difluoro-γ-lactam derivatives†","authors":"","doi":"10.1039/d4ob01012d","DOIUrl":"10.1039/d4ob01012d","url":null,"abstract":"<div><p>Herein, an N-heterocyclic carbene (NHC) catalyzed radical tandem cyclization reaction of <em>N</em>-allylbromodifluoroacetamides and aldehydes has been developed. This method is an efficient protocol for synthesizing α,α-difluoro-γ-lactam derivatives in moderate to good yields (27 examples, up to 88% yield and 10 : 1 dr). This strategy features mild and metal-free conditions, high efficiency, and a broad substrate scope.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141974513","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Biosynthesis of brevinic acid from lawsone† 从律酮中生物合成布来维酸。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01184h
{"title":"Biosynthesis of brevinic acid from lawsone†","authors":"","doi":"10.1039/d4ob01184h","DOIUrl":"10.1039/d4ob01184h","url":null,"abstract":"<div><p>The menaquinone-pathway (men) is widespread in bacteria and key to the biosynthesis of intriguing small molecules such as the essential vitamin menaquinone and the natural dye lawsone. The violet molecule brevinic acid is another proposed product of men, but its direct biosynthetic precursor has remained doubtful. In this study, we isolated brevinic acid from <em>E. coli</em> and confirmed its non-enzymatic formation from lawsone and homocysteine involving an intermediate acetylation or phosphorylation step. We furthermore compared our proposed substrates in a non-enzymatic assay against the previously hypothesized precursor DHNA and showed that the reaction with activated lawsone derivatives proceeded faster, more selective, and with complete turnover. This supports our proposed biosynthesis of brevinic acid from lawsone and enables a cost effective, larger-scale synthesis of brevinic acid.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photochemical tandem reaction of nitrogen containing heterocycles, bicyclo[1.1.1]pentane, and difluoroiodane(iii) reagents† 含氮杂环、双环[1.1.1]戊烷和二氟碘烷（III）试剂的光化学串联反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01020e
{"title":"Photochemical tandem reaction of nitrogen containing heterocycles, bicyclo[1.1.1]pentane, and difluoroiodane(iii) reagents†","authors":"","doi":"10.1039/d4ob01020e","DOIUrl":"10.1039/d4ob01020e","url":null,"abstract":"<div><p>A visible light-induced difluoroalkylation/heteroarylation of [1.1.1]propellane with nitrogen containing heterocycles and difluoroiodane(<span>iii</span>) reagents was achieved. Various heteroarenes and difluoroiodane(<span>iii</span>) reagents exhibited good compatibility, yielding the desired products in moderate to good yields. The accessibility of the reagents and the mild reaction conditions establish this method as an alternative and practical strategy for accessing diverse 1-difluoroalkyl-3-heteroaryl bicyclo[1.1.1]pentanes (BCPs).</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981261","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent development in the synthesis of imidazo[1,5-a]indole derivatives: an in-depth overview 咪唑并[1,5-a]吲哚衍生物合成的最新进展：深入综述。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/D4OB01131G
Elizabeth J. Diana, Jisna Jose and Thomas V. Mathew
{"title":"Recent development in the synthesis of imidazo[1,5-a]indole derivatives: an in-depth overview","authors":"Elizabeth J. Diana, Jisna Jose and Thomas V. Mathew","doi":"10.1039/D4OB01131G","DOIUrl":"10.1039/D4OB01131G","url":null,"abstract":"<p >In the realm of nitrogen-fused heterocycles, imidazo[1,5-<em>a</em>]indole and its derivatives are recognized as privileged structural patterns in various pharmaceutical drugs and biologically active natural products, emphasizing their significance. This review comprehensively explores the synthetic strategies for constructing imidazo[1,5-<em>a</em>]indole scaffolds, with a particular focus on transition metal-catalyzed methodologies. The primary highlighted method is [4 + 1] annulation, along with other notable approaches such as C–H activation/cyclization, enantioselective C–H annulation, intramolecular hydroamination, and double cyclization processes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142078521","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Formation of cyclopenta[c]quinolines through visible-light-induced photoredox cascade bis-annulations of 1,7-enynes with sulfoxonium ylides† 在可见光诱导下，1,7-烯炔与亚磺鎓酰化物发生光氧化级联反应，生成环戊并[c]喹啉。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/D4OB01294A
Ning Xian, Guo-Jun Deng and Huawen Huang
{"title":"Formation of cyclopenta[c]quinolines through visible-light-induced photoredox cascade bis-annulations of 1,7-enynes with sulfoxonium ylides†","authors":"Ning Xian, Guo-Jun Deng and Huawen Huang","doi":"10.1039/D4OB01294A","DOIUrl":"10.1039/D4OB01294A","url":null,"abstract":"<p >A novel visible-light-driven photoredox-catalyzed cascade bicyclization of 1,7-enynes with aqueous sulfoxonium ylides is reported. The reaction is highly chemoselective with three new C–C bonds, two new rings, and an all-carbon quaternary stereocenter constructed in a one-pot fashion. This mild protocol features a remarkably broad substrate scope with good functional group tolerance, providing a general and practical approach to access various cyclopenta[<em>c</em>]quinolines.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102248","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ring-closing metathesis of dialkenylcycloalkanes for the synthesis of fused bicycloalkanes and tricycloalkanes† 二烯基环烷烃的闭环偏析合成融合双环烷烃和三环烷烃。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01143k
{"title":"Ring-closing metathesis of dialkenylcycloalkanes for the synthesis of fused bicycloalkanes and tricycloalkanes†","authors":"","doi":"10.1039/d4ob01143k","DOIUrl":"10.1039/d4ob01143k","url":null,"abstract":"<div><p>Ring-closing metathesis of dialkenyldisilacycloalkane using the Grubbs catalyst, followed by hydrogenation, afforded a mixture of two disilabicycloalkanes and tetrasilatricycloalkanes. This method can synthesize a diastereomer mixture of disilabicycloalkanes with one differing alkyl side chain. The observed symmetries of the NMR spectra of <em>anti</em>-bicycloalkanes depend significantly on the length of the side chain. The findings may contribute to the molecular design of functional bicycloalkanes based on structural transformations of the stable forms.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141915517","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nickel-catalysed reductive C–N bond cross-coupling between aryl halides and N-chloroamides† 镍催化的芳基卤化物与 N-氯酰胺之间的还原性 C-N 键交叉耦合。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob00970c
{"title":"Nickel-catalysed reductive C–N bond cross-coupling between aryl halides and N-chloroamides†","authors":"","doi":"10.1039/d4ob00970c","DOIUrl":"10.1039/d4ob00970c","url":null,"abstract":"<div><p>A method for the direct synthesis of <em>N</em>-aryl lactams and amides with aryl halides and <em>N</em>-chloroamides through a Ni-catalyzed reductive C–N coupling reaction has been developed. The reaction features the advantages of mild conditions, good functional group tolerance and broad substrate scope including drug-derived substrates, and also provided direct access to the key synthetic intermediates for some bioactive molecules, suggesting the practicability of this method. Finally, DFT calculations were performed to shed further light on the reaction mechanism and it was found that an amidyl radical might be involved.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141970081","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Copper-catalyzed deborodeuteration of arylboronic acids/borates using D2O as the deuterium source† 使用 D2O 作为氘源，铜催化芳基硼酸/硼酸盐的脱硼脱碘反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/D4OB01251H
Mingqi Yang, Tao Chen, Ze-Feng Xu, Mingming Yu and Chuan-Ying Li
{"title":"Copper-catalyzed deborodeuteration of arylboronic acids/borates using D2O as the deuterium source†","authors":"Mingqi Yang, Tao Chen, Ze-Feng Xu, Mingming Yu and Chuan-Ying Li","doi":"10.1039/D4OB01251H","DOIUrl":"10.1039/D4OB01251H","url":null,"abstract":"<p >A straightforward copper-catalyzed deborodeuteration of arylboronic acids and borates was achieved, employing the cost-effective deuterium source D<small><sub>2</sub></small>O. This protocol demonstrates wide substrate applicability, exceptional deuterium incorporation efficiency, and favorable tolerance for various functional groups. Therefore, this approach offers a mild option for further applications in valuable deuterium molecule synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102245","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Selectively lighting up glyoxal in living cells using an o-phenylenediamine fused hemicyanine† 利用邻苯二胺融合半氰胺选择性地点亮活细胞中的乙二醛。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01195c
{"title":"Selectively lighting up glyoxal in living cells using an o-phenylenediamine fused hemicyanine†","authors":"","doi":"10.1039/d4ob01195c","DOIUrl":"10.1039/d4ob01195c","url":null,"abstract":"<div><p>Glyoxal (GL) is a reactive α-dicarbonyl compound generated from glycated proteins in the Maillard reaction. It has attracted particular attention over the past few years because of its possible clinical significance in chronic and age-related diseases. In this work, a reaction-based red emission fluorescent probe <strong>GL1</strong> has been synthesized successfully by grafting an alkyl group onto an amino group to regulate its selectivity for GL. Under physiological conditions, the fluorescence intensity of <strong>GL1</strong> at 640 nm obviously increased with the increase of GL concentration, and it exhibited high selectivity for GL over other reactive carbonyl compounds, as well as a lower detection limit (0.021 μM) and a larger Stokes shift (112 nm). At the same time, <strong>GL1</strong> can selectively accumulate in mitochondria and can be used to detect exogenous and endogenous GL in living cells with low cytotoxicity.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141905079","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of aryl enopyranones directly from glycals and aromatic halides to access 2-deoxy-β-C-aryl glycosides† 直接从甘油和芳香卤化物合成芳基烯丙酮，从而获得 2-脱氧-β-C-芳基苷。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01172d
{"title":"Synthesis of aryl enopyranones directly from glycals and aromatic halides to access 2-deoxy-β-C-aryl glycosides†","authors":"","doi":"10.1039/d4ob01172d","DOIUrl":"10.1039/d4ob01172d","url":null,"abstract":"<div><p>An efficient synthesis of aryl enopyranones <em>via</em> an oxidative Heck-type coupling reaction between ether protected <span>d</span>/<span>l</span>-glycals and different aryl halides is developed. This one-step method attaches an aryl group at the C-1 position keeping the C-1/C-2 double bond intact <em>via</em> the Saegusa–Ito type oxidation, thus facilitating the synthesis of medicinally important 2-deoxy-β-aryl-C-glycosides after Pd/C reduction.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141905080","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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