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P-Stereodefined morpholino dinucleoside 3',5'-phosphorothioates. P-Stereodefined morpholino dinucleoside 3',5'-phosphorothioates.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-11 DOI: 10.1039/d4ob01437e
Katarzyna Jastrzębska, Patrycja Antończyk, Rafał Dolot
{"title":"P-Stereodefined morpholino dinucleoside 3',5'-phosphorothioates.","authors":"Katarzyna Jastrzębska, Patrycja Antończyk, Rafał Dolot","doi":"10.1039/d4ob01437e","DOIUrl":"https://doi.org/10.1039/d4ob01437e","url":null,"abstract":"<p><p>Here, we present for the first time the synthesis of P-stereodefined morpholino phosphorothioate analogs by using a modified 1,3,2-oxathiaphospholane method (OTP method) and provide valuable structural insights into their stereochemistry. <i>N</i>-(2-Thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) derivatives of morpholino-type nucleosides (<i>m</i>U-OTPs) were synthesized, separated into pure P-diastereomers and used to prepare P-stereodefined morpholino dinucleoside 3',5'-phosphorothioates.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398752","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 N-heterocyclic amides from imidazoheterocycles through convergent paired electrolysis. 通过会聚成对电解法从咪唑杂环合成 N-杂环酰胺。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-11 DOI: 10.1039/d4ob01115e
Elise Leclercq, Laura Chevet, Nicolas David, Muriel Durandetti, Laëtitia Chausset-Boissarie
{"title":"Synthesis of N-heterocyclic amides from imidazoheterocycles through convergent paired electrolysis.","authors":"Elise Leclercq, Laura Chevet, Nicolas David, Muriel Durandetti, Laëtitia Chausset-Boissarie","doi":"10.1039/d4ob01115e","DOIUrl":"https://doi.org/10.1039/d4ob01115e","url":null,"abstract":"<p><p>An efficient ring opening of imidazoheterocycles induced by a direct C-H azidation resulting in an unusual formation of N-heterocyclic amides has been successfully developed through convergent paired electrolysis. A broad scope of pyridylbenzamides could be obtained in moderate to excellent yields under exogenous-oxidant, electrolyte- and metal-free electrochemical conditions. The methodology was transferred to continuous flow conditions resulting in notable improvements particularly in terms of cost-efficiency over traditional batch versions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398753","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 ω-functionalized ketones from strained cyclic alcohols by ring-opening and cross-recombination between alkyl and N-oxyl radicals. 通过烷基和 N-氧自由基之间的开环和交叉再结合，从应变环醇合成ω-官能化酮。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-10 DOI: 10.1039/d4ob01490a
Alexander S Budnikov, Igor B Krylov, Mikhail I Shevchenko, Lyubov' L Sokova, Yan Liu, Bing Yu, Alexander O Terent'ev
{"title":"Synthesis of ω-functionalized ketones from strained cyclic alcohols by ring-opening and cross-recombination between alkyl and <i>N</i>-oxyl radicals.","authors":"Alexander S Budnikov, Igor B Krylov, Mikhail I Shevchenko, Lyubov' L Sokova, Yan Liu, Bing Yu, Alexander O Terent'ev","doi":"10.1039/d4ob01490a","DOIUrl":"https://doi.org/10.1039/d4ob01490a","url":null,"abstract":"<p><p>Radical ring-opening oxyimidation of cyclobutanols and cyclopropanols with the formation of ω-functionalized ketones was discovered. The oxidative C-O coupling proceeds <i>via</i> the interception of a primary alkyl radical generated from a cyclic alcohol with a reactive radical generated <i>in situ</i>, which is an electron-deficient <i>N</i>-oxyl radical. The developed conditions allow for the balanced generation rates of carbon- and <i>N</i>-oxyl radicals, which are necessary for their selective cross-recombination. Thus, typical competitive dimerization processes of carbon-centered radicals, their intermolecular cyclization, and <i>N</i>-oxyl radical self-decay are suppressed. The method is applicable to a wide range of cyclobutanols and results in oxyimidated ketones in yields of up to 82%.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386471","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
Anion recognition using meta-substituted ureidocalix[4]arene receptors. 利用元取代的尿醛[4]炔受体识别阴离子。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-09 DOI: 10.1039/d4ob01441c
A Surina, J Čejka, K Salvadori, P Lhoták
{"title":"Anion recognition using <i>meta</i>-substituted ureidocalix[4]arene receptors.","authors":"A Surina, J Čejka, K Salvadori, P Lhoták","doi":"10.1039/d4ob01441c","DOIUrl":"https://doi.org/10.1039/d4ob01441c","url":null,"abstract":"<p><p>Calix[4]arenes bearing urea units at the <i>meta</i> position(s) of the upper rim of the macrocyclic skeleton were prepared by the reaction of the corresponding amines with aryl isocyanates. As shown by the <sup>1</sup>H NMR and UV/vis titration experiments, these systems are capable of effectively complexing selected anions even in a highly competitive environment (such as DMSO-<i>d</i><sub>6</sub>). While the monoureido derivatives showed approximately the same complexation ability irrespective of the substitution (<i>para vs. meta</i> isomers), the bisureas at the upper rim demonstrated interesting differences in complexation. The <i>meta</i>,<i>meta</i> and <i>para</i>,<i>para</i> isomers were shown to prefer 2 : 1 complexes (anion : receptor) regardless of the anion tested, while the analogous <i>meta</i>,<i>para</i> isomer formed 1 : 1 complexes with strongly coordinated anions (<i>e.g.</i> H<sub>2</sub>PO<sub>4</sub><sup>-</sup>) based on synchronous complexation by both ureido groups. This suggests that the regioselective introduction of urea units into the upper rim of calix[4]arene brings with it the possibility of \"tuning\" the complexation properties depending on the substitution pattern of the functional groups.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386467","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
A clickable coenzyme A derived probe for investigating phosphopantetheinyl transferase activity in natural product biosynthesis. 一种可点击的辅酶 A 衍生物探针，用于研究天然产物生物合成过程中磷酸泛乙烯基转移酶的活性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-09 DOI: 10.1039/d4ob01485e
Zhiyong Yin, Houchao Xu, Jeroen S Dickschat
{"title":"A clickable coenzyme A derived probe for investigating phosphopantetheinyl transferase activity in natural product biosynthesis.","authors":"Zhiyong Yin, Houchao Xu, Jeroen S Dickschat","doi":"10.1039/d4ob01485e","DOIUrl":"https://doi.org/10.1039/d4ob01485e","url":null,"abstract":"<p><p>Phosphopantetheinyl transferases activate carrier proteins through attachment of a coenzyme A derived phosphopantetheinyl linker. This study describes a method to monitor this process through a modified HSCoA with an alkyne group, allowing for the Cu-catalysed alkyne-azide cycloaddition of a fluorescent tag. Application of the method in an enzyme screening resulted in the identification of new promiscuous PPTases.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386466","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
One-pot synthesis of N-sulfonylamidines from N-acylsulfonamides enabled by a metal triflate-mediated nonhydrolytic N-deacylation. 通过金属三late 介导的非水解 N-脱酰基反应，从 N-酰基磺酰胺中一次性合成 N-磺酰胺。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-09 DOI: 10.1039/d4ob01296h
Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu, Dayong Sang
{"title":"One-pot synthesis of <i>N</i>-sulfonylamidines from <i>N</i>-acylsulfonamides enabled by a metal triflate-mediated nonhydrolytic <i>N</i>-deacylation.","authors":"Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu, Dayong Sang","doi":"10.1039/d4ob01296h","DOIUrl":"https://doi.org/10.1039/d4ob01296h","url":null,"abstract":"<p><p>A triflate salt-catalyzed nonhydrolytic method for the deacylation of <i>N</i>-acylsulfonamides and subsequent one-pot condensation of the newly formed sulfonamides with <i>N</i>,<i>N</i>-dimethylformamide dimethyl acetal to provide <i>N</i>-sulfonylamidines is presented. A range of aliphatic and aromatic <i>N</i>-acylsulfonamides bearing various <i>N</i>-acyl groups such as acetyl, propionyl, butyrl, isobutyryl, octanoyl, benzoyl, 2-phenylacetyl, and sterically hindered pivaloyl are readily transformed into the corresponding <i>N</i>-sulfonylamidines in good to excellent yields. A variety of functional groups including halogeno, keto, nitro, cyano, hydroxyl, ether, and carboxylic ester are tolerated intact.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386469","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
Photocatalyst-free regioselective sulfonamidation of N-(2-hydroxyaryl)amides in visible-light. 可见光下 N-(2-羟基芳基)酰胺的无光催化剂区域选择性磺酰胺化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-08 DOI: 10.1039/d4ob01393j
Rajat, Shruti Rajput, Nitika Grover, Nidhi Jain
{"title":"Photocatalyst-free regioselective sulfonamidation of <i>N</i>-(2-hydroxyaryl)amides in visible-light.","authors":"Rajat, Shruti Rajput, Nitika Grover, Nidhi Jain","doi":"10.1039/d4ob01393j","DOIUrl":"https://doi.org/10.1039/d4ob01393j","url":null,"abstract":"<p><p>In this work, we report a regioselective sulfonamidation of <i>N</i>-(2-hydroxyaryl)amides with iminoiodinanes and iodine in visible light at room temperature. The method does not require a strong oxidant, metal or photocatalyst and enables direct functionalization of a C-H bond to a C-N bond. Mechanistic investigations suggest <i>in situ</i> generation of an N-centered radical from <i>N</i>,<i>N</i>-diiodo-sulfonamide by homolytic N-I bond cleavage followed by its site-specific addition to <i>N</i>-(2-hydroxyaryl)amides to furnish <i>para</i>-sulfonamide derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386470","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
Transition-metal-free iterative two-fold reductive coupling and 1,3-borotropic shift to form 1,4-skipped dienes. 无过渡金属迭代双倍还原耦合和 1,3-borotropic 移位形成 1,4-skipped 二烯。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-08 DOI: 10.1039/d4ob01389a
Kasarla Varalaxmi, Kangkan Pradhan, Hasina Mamataj Begam, Arghya Polley, Deepak Kumar, Ranjan Jana
{"title":"Transition-metal-free iterative two-fold reductive coupling and 1,3-borotropic shift to form 1,4-skipped dienes.","authors":"Kasarla Varalaxmi, Kangkan Pradhan, Hasina Mamataj Begam, Arghya Polley, Deepak Kumar, Ranjan Jana","doi":"10.1039/d4ob01389a","DOIUrl":"https://doi.org/10.1039/d4ob01389a","url":null,"abstract":"<p><p>We report herein a transition-metal-free two-fold reductive coupling between prenal (allyl) tosylhydrazone and boronic acids/1,3-borotropic shift cascade to furnish 1,4-skipped dienes. In this work, a single batch operation produces (<i>E</i>,<i>E</i>)-1,4-skipped dienes by undergoing a second reductive coupling of the transient boronic acid, which developed <i>in situ</i> following the first reductive allylation and a cascade 1,3-boron migration. Remarkably, the protocol is compatible with various aryl- and alkyl-substituted boronic acids, is scalable and has demonstrated on 61 substrates with yields up to 98%.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386472","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(II) quinoxolinol imidazolium complexes in catalytic oxidation of benzylic and heterocyclic alcohols. 铜（II）喹喔啉咪唑鎓络合物在催化氧化苄醇和杂环醇中的作用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-08 DOI: 10.1039/d4ob01081g
Xiaoyu Huo, Mariano Guagliardo, Anne E V Gorden
{"title":"Copper(II) quinoxolinol imidazolium complexes in catalytic oxidation of benzylic and heterocyclic alcohols.","authors":"Xiaoyu Huo, Mariano Guagliardo, Anne E V Gorden","doi":"10.1039/d4ob01081g","DOIUrl":"https://doi.org/10.1039/d4ob01081g","url":null,"abstract":"<p><p>A novel copper(II) quinoxolinol complex has been prepared using a condensation reaction based on previous studies. The copper(II) quinoxolinol salen complex has been applied as a catalyst using <i>tert</i>-butyl hydroperoxide (TBHP) as the oxidant, demonstrating that benzylic and heterocyclic alcohols can be converted efficiently to the corresponding aldehydes. Excellent yields can be achieved (up to 99%) within a short reaction time and with great tolerance for functional groups.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386468","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
Well-defined cobalt(II)-catalyzed synthesis of perimidine derivatives via acceptorless dehydrogenative annulation. 在钴(II)催化下，通过无受体脱氢环化合成明确的包嘧啶衍生物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-08 DOI: 10.1039/d4ob01306a
Debjyoti Pal, Rajashri Sarmah, Avijit Mondal, Itu Mallick, Dipankar Srimani
{"title":"Well-defined cobalt(II)-catalyzed synthesis of perimidine derivatives <i>via</i> acceptorless dehydrogenative annulation.","authors":"Debjyoti Pal, Rajashri Sarmah, Avijit Mondal, Itu Mallick, Dipankar Srimani","doi":"10.1039/d4ob01306a","DOIUrl":"https://doi.org/10.1039/d4ob01306a","url":null,"abstract":"<p><p>The versatility of the perimidine moiety offers a rich playground for researchers in fields ranging from medical science to industrial chemistry. Herein, we describe the first Co-catalyzed synthesis of 2,3-dihydro-1<i>H</i>-perimidine <i>via</i> acceptorless dehydrogenative annulation (ADA). Apart from featuring benzyl alcohol having different functionalities, heteroaryl and aliphatic alcohols also provide good yields. Our catalytic protocol is also suitable for different fatty alcohols for furnishing perimidine derivatives, keeping distal unsaturation intact. Several kinetic and control tests were carried out in order to understand the reaction sequence.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386474","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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