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Quantum chemical study on the activity of organic superbase phosphazene t-Bu-P4/DMSO in the autocondensation reaction of ketones 酮类自缩合反应中有机超碱磷腈t-Bu-P4/DMSO活性的量子化学研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-08 DOI: 10.1016/j.tetlet.2025.155738
Vladimir B. Orel , Anastasia A. Manzhueva , Nikita V. Teplyashin
{"title":"Quantum chemical study on the activity of organic superbase phosphazene t-Bu-P4/DMSO in the autocondensation reaction of ketones","authors":"Vladimir B. Orel ,&nbsp;Anastasia A. Manzhueva ,&nbsp;Nikita V. Teplyashin","doi":"10.1016/j.tetlet.2025.155738","DOIUrl":"10.1016/j.tetlet.2025.155738","url":null,"abstract":"<div><div>This theoretical work is devoted to the study on the activity of phosphazene <em>t</em>-Bu-P4/DMSO in the autocondensation reaction of ketones, which is often an undesirable side process in base-promoted reactions involving ketones. It is shown that the 4-hydroxyenolate stabilized by the phosphazenium cation <em>t</em>-Bu-P4H<sup>+</sup> is thermodynamically and kinetically most stable in the <em>t</em>-Bu-P4/DMSO system among the condensation products of two acetone molecules. The remaining condensation products are formed only with a slight decrease in free energy. Possible condensation of a larger number of ketone molecules is hindered due to the high barrier and disadvantageous formation of 4-methylpent-3-en-2-one. The formation of the 4-hydroxyenolate from acetone is associated with activation energies greater than the activation energy of the reaction of acetone ethynylation with phenylacetylene. As a result, the use of the <em>t</em>-Bu-P4/DMSO system minimizes or eliminates the formation of ketone condensation by-products in ethynylation reactions. In cascade assemblies of acetylenes with ketones, carried out under more severe conditions, only ketols can be expected as condensation by-products.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155738"},"PeriodicalIF":1.5,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144605262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
N-cyano-N-phenyl-p-toluenesulfonamide as electrophilic nitrile source for the synthesis of oxadiazoles n -氰基- n -苯基-对甲苯磺酰胺作为亲电腈源合成恶二唑
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-07 DOI: 10.1016/j.tetlet.2025.155725
Talita B. Gontijo, Eufrânio N. da Silva Júnior, Mariana Guerra de Aguilar, Rossimiriam P. de Freitas
{"title":"N-cyano-N-phenyl-p-toluenesulfonamide as electrophilic nitrile source for the synthesis of oxadiazoles","authors":"Talita B. Gontijo,&nbsp;Eufrânio N. da Silva Júnior,&nbsp;Mariana Guerra de Aguilar,&nbsp;Rossimiriam P. de Freitas","doi":"10.1016/j.tetlet.2025.155725","DOIUrl":"10.1016/j.tetlet.2025.155725","url":null,"abstract":"<div><div>A streamlined protocol for the synthesis of amino-1,3,4-oxadiazole heterocycles using NCTS (<em>N</em>-cyano-<em>N</em>-phenyl-<em>p</em>-toluenesulfonamide) as a less toxic and easy-to-handle electrophilic nitrile source, in combination with hydrazides, has been developed. This novel methodology enables the synthesis of amino-1,3,4-oxadiazole derivatives bearing both electron-donating and electron-withdrawing substituents in fewer steps, with improved operational simplicity and yields ranging from 42 % to 70 %. Although several methodologies for the synthesis of amino-1,3,4-oxadiazoles have been reported, our approach offers significant advantages in terms of efficiency, safety, and environmental impact.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155725"},"PeriodicalIF":1.5,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144570345","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Scalable route to high-purity 17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid, an intermediate for therapeutic peptide synthesis 高纯度17-氨基-10-氧-3,6,12,15-四氧-9-氮杂庚烷酸的可扩展途径，用于治疗性肽合成的中间体
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-04 DOI: 10.1016/j.tetlet.2025.155730
Jae Hoon Jeon , Dong Wook Kang
{"title":"Scalable route to high-purity 17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid, an intermediate for therapeutic peptide synthesis","authors":"Jae Hoon Jeon ,&nbsp;Dong Wook Kang","doi":"10.1016/j.tetlet.2025.155730","DOIUrl":"10.1016/j.tetlet.2025.155730","url":null,"abstract":"<div><div>Herein, we report a method for the scalable, high-purity production of 17-amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid, a crucial intermediate in the production of peptide therapeutics such as semaglutide and tirzepatide. Existing synthetic methods for the target compound have limitations such as high-impurity content, poor yield, and complex purification steps. Our new synthetic route, which incorporates benzotriazole, provides enhanced stability and improved crystallization. Crucially, we achieved a purity above 99.7 %, demonstrating economic viability and efficiency for large-scale commercial production.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155730"},"PeriodicalIF":1.5,"publicationDate":"2025-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144587420","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
From tetrachlorinated perylene diimide cyclophanes to sila-annulated high-affinity receptors 从四氯化苝二亚胺环番到硅环高亲和受体
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-03 DOI: 10.1016/j.tetlet.2025.155729
Bai-Yang Qian , Bi-Lian Chai , Jianbin Lin, Hui-Jun Zhang
{"title":"From tetrachlorinated perylene diimide cyclophanes to sila-annulated high-affinity receptors","authors":"Bai-Yang Qian ,&nbsp;Bi-Lian Chai ,&nbsp;Jianbin Lin,&nbsp;Hui-Jun Zhang","doi":"10.1016/j.tetlet.2025.155729","DOIUrl":"10.1016/j.tetlet.2025.155729","url":null,"abstract":"<div><div>We present the design and synthesis of two novel tetrachlorinated perylene diimide (PDI) cyclophanes. Using the tetrachloro-PDI cyclophane as a precursor, a silicon-annulated PDI cyclophane was readily synthesized via an eight-fold palladium-catalyzed coupling strategy. Host-guest interaction studies demonstrate that the resulting sila-PDI cyclophane effectively binds π-conjugated molecules, such as electron-rich anthracene (<strong>AN</strong>) and electron-poor anthraquinone (<strong>AQ</strong>). Notably, the binding constant for the structurally well-defined <strong>AQ</strong>⊂sila-PDI cyclophane complex is as high as <em>K</em><sub>a</sub> = (1.04 ± 0.22) × 10<sup>6</sup> M<sup>−1</sup>, highlighting its strong affinity. This study underscores the potential utility of tetrachloro-PDI cyclophanes as modular platforms for constructing various heteroannulated architectures.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155729"},"PeriodicalIF":1.5,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144614852","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 novel CoF3-mediated fluorination approach toward crystalline perthiolated coronenes 一种新的cof3介导的结晶过硫化冕的氟化方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-07-03 DOI: 10.1016/j.tetlet.2025.155728
Sven Mörsel , Frank Hampel , Andreas Hirsch
{"title":"A novel CoF3-mediated fluorination approach toward crystalline perthiolated coronenes","authors":"Sven Mörsel ,&nbsp;Frank Hampel ,&nbsp;Andreas Hirsch","doi":"10.1016/j.tetlet.2025.155728","DOIUrl":"10.1016/j.tetlet.2025.155728","url":null,"abstract":"<div><div>We describe the cobalt-mediated solid-state fluorination of coronene. The transition-metal-mediated fluorination facilitates perfluorination and dearomatization only at the edges of the molecule, leaving the aromatic core intact. The resulting edge-perfluorinated coronene serves as a precursor for the microwave-assisted synthesis of dodecakis-(phenylthio)coronene. Single crystal X-ray structure analysis of dodecakis-(phenylthio)coronene reveals a columnar alignment, facilitated only by short CH<img>π interactions and CH<img>S hydrogen bonding.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155728"},"PeriodicalIF":1.5,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144623605","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Iron-catalyzed 1,2-diketone synthesis via benzoin condensation/oxidation in water 铁催化苯并安息香缩合/水中氧化合成1,2-二酮
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-29 DOI: 10.1016/j.tetlet.2025.155717
Tsukasa Inishi, Toshitaka Okamura, Takashi Nishikata
{"title":"Iron-catalyzed 1,2-diketone synthesis via benzoin condensation/oxidation in water","authors":"Tsukasa Inishi,&nbsp;Toshitaka Okamura,&nbsp;Takashi Nishikata","doi":"10.1016/j.tetlet.2025.155717","DOIUrl":"10.1016/j.tetlet.2025.155717","url":null,"abstract":"<div><div>In this study, we have developed a methodology for the synthesis of 1,2-diketones via aerobic oxidation of benzaldehyde derivatives in water using N-heterocyclic carbene (NHC) catalysis. This approach involves a two-step one-pot process: benzoin condensation catalyzed by NHC, followed by FeS-catalyzed aerobic oxidation. By employing water as the reaction medium with Triton X as a surfactant, we have established an environmentally benign reaction system that eliminates the need for organic solvents. Through a series of control experiments, we have elucidated the roles of the NHC catalyst and FeS in the reaction mechanism.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155717"},"PeriodicalIF":1.5,"publicationDate":"2025-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144517359","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
K2S2O8/TFA-mediated [3+2+1] synthesis of substituted quinolines from anilines and alcohols using DMSO as a C1 source 以二甲基亚砜为C1源，K2S2O8/ tfa介导[3+2+1]苯胺和醇合成取代喹啉
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-28 DOI: 10.1016/j.tetlet.2025.155724
Zhipin Wang, Zheng Li
{"title":"K2S2O8/TFA-mediated [3+2+1] synthesis of substituted quinolines from anilines and alcohols using DMSO as a C1 source","authors":"Zhipin Wang,&nbsp;Zheng Li","doi":"10.1016/j.tetlet.2025.155724","DOIUrl":"10.1016/j.tetlet.2025.155724","url":null,"abstract":"<div><div>An efficient K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/TFA-mediated [3+2+1] cycloadditions of readily available anilines, primary alcohols/secondary alcohols, and DMSO is described. This method allows the direct and highly effective synthesis of privileged quinolones, such as 3-arylquinolines and 4-arylquinolines, with exclusive regioselectivity and good functional group tolerance in good to excellent yield. DMSO is employed as the C1 building block of quinoline products, the oxidant, and the solvent. The possible reaction mechanism is also discussed. The method can also be extended to a gram scale.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155724"},"PeriodicalIF":1.5,"publicationDate":"2025-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510883","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 for polycyclic spirooxindoles via base promoted spiroannulation reaction of cyclic β-enaminones and MBH maleimides of isatins 碱促进环β-胺酮和isatins的MBH马来酰亚胺的旋环反应合成多环螺旋体吲哚
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-27 DOI: 10.1016/j.tetlet.2025.155720
Shao-Cong Zhan, Zi-Ying Xiao, Jing Sun, Chao-Guo Yan
{"title":"Synthesis for polycyclic spirooxindoles via base promoted spiroannulation reaction of cyclic β-enaminones and MBH maleimides of isatins","authors":"Shao-Cong Zhan,&nbsp;Zi-Ying Xiao,&nbsp;Jing Sun,&nbsp;Chao-Guo Yan","doi":"10.1016/j.tetlet.2025.155720","DOIUrl":"10.1016/j.tetlet.2025.155720","url":null,"abstract":"<div><div>An efficient synthetic protocol for polycyclic spirooxindoles was developed by base promoted spiroannulation reaction of cyclic <em>β</em>-enaminones and MBH maleimides of isatins in acetonitrile at elevated temperature. This reaction not only afforded functionalized spiro[indoline-3,9′-pyrrolo[3,4-<em>b</em>]quinoline]-1′,2,3′,8′-tetraones in satisfactory yields via spiroannulation reaction, but also gave unexpected dihydrospiro[indoline-3,9′-pyrrolo[3,4-<em>b</em>]quinoline]-1′,2,3′,8′-tetraone derivatives via further rearrangement process. The chemical structures of the two kinds of the spirooxindoles were confirmed by X-ray diffraction single crystal determination.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155720"},"PeriodicalIF":1.5,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144492067","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Efficient synthesis of chlorinated Dihydronaphthalene derivatives using N,N-diisopropylformamide-POCl3 as a Vilsmeier reagent 以N，N-二异丙基甲酰胺- pocl3为维斯迈试剂高效合成氯化二氢萘衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-27 DOI: 10.1016/j.tetlet.2025.155726
Dinghao Li , Junwei Li , Yumeng Zhang, Fang-Lin Zhang
{"title":"Efficient synthesis of chlorinated Dihydronaphthalene derivatives using N,N-diisopropylformamide-POCl3 as a Vilsmeier reagent","authors":"Dinghao Li ,&nbsp;Junwei Li ,&nbsp;Yumeng Zhang,&nbsp;Fang-Lin Zhang","doi":"10.1016/j.tetlet.2025.155726","DOIUrl":"10.1016/j.tetlet.2025.155726","url":null,"abstract":"<div><div>A newly developed chlorinating reagent (<em>N,N</em>-diisopropylformamide-POCl<sub>3</sub> complex) and metal halide (ZnCl<sub>2</sub>) synergistic reaction system was reported for the efficient chlorination of polysubstituted 1-tetralones. This protocol facilitates the reaction to proceed under mild conditions with this in situ formed Vilsmeier reagent, and a broad substrate scope could be compatible. 28 examples were successfully converted to the corresponding chlorodihydronaphthalenes in moderate to good yields, meanwhile significantly suppressing the formation of halogenated enal byproducts. The simplicity, high efficiency and wide substrate compatibility enable this new method to be a promising alternative for the synthesis of halogenated aryl olefins and drug molecules.</div><div>2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155726"},"PeriodicalIF":1.5,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144570344","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides [Ni(PnBu3)2Cl2]作为经济预催化剂用于芳基磺酸酯与卤化物的Suzuki-Miyaura交叉偶联反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-24 DOI: 10.1016/j.tetlet.2025.155723
Eric Fortin Constant, Armaan Grewal, Eric C. Keske
{"title":"[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides","authors":"Eric Fortin Constant,&nbsp;Armaan Grewal,&nbsp;Eric C. Keske","doi":"10.1016/j.tetlet.2025.155723","DOIUrl":"10.1016/j.tetlet.2025.155723","url":null,"abstract":"<div><div>The air stable precatalyst [Ni(PnBu<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] was successfully demonstrated to be highly active in the Suzuki-Miyaura reaction of aryl tosylates, mesylates and chlorides without the use of an external reducing agent. Biaryl products were typically formed in high yield without the requirement of large excesses of phenyl boronic acid derivatives or base. This precatalyst can be readily prepared from inexpensive starting materials representing a distinct economic advantage over previously reported precatalysts. We further report our computational studies indicating potential oxidative addition mechanisms with this precatalyst on aryl sulfonate electrophiles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155723"},"PeriodicalIF":1.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144556706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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