Tetrahedron chem最新文献_第4页

Self-assembly via hydrogen bonding of bis(18-crown-6)-1,3-distyrylbenzene and [2 + 2] photocycloaddition: Stereoselective synthesis of [2.2]metacyclophanes and butterfly-type thermal isomerization 双(18-冠-6)-1,3-二苯乙烯通过氢键自组装和[2 + 2]光环加成：2.2]metacyclophanes 的立体选择性合成和蝶式热异构化

Tetrahedron chem Pub Date : 2024-08-18 DOI: 10.1016/j.tchem.2024.100091

Timofey P. Martyanov , Artem P. Vorozhtsov , Evgeny N. Ushakov , Nikita A. Slesarenko , Ilia V. Sulimenkov , Sergey P. Gromov

{"title":"Self-assembly via hydrogen bonding of bis(18-crown-6)-1,3-distyrylbenzene and [2 + 2] photocycloaddition: Stereoselective synthesis of [2.2]metacyclophanes and butterfly-type thermal isomerization","authors":"Timofey P. Martyanov , Artem P. Vorozhtsov , Evgeny N. Ushakov , Nikita A. Slesarenko , Ilia V. Sulimenkov , Sergey P. Gromov","doi":"10.1016/j.tchem.2024.100091","DOIUrl":"10.1016/j.tchem.2024.100091","url":null,"abstract":"<div>The photochemistry of bis(18-crown-6)-containing 1,3-distyrylbenzene and its 2 : 2 bis-pseudo-sandwich complex with ethane-1,2-diammonium was studied. The UV irradiation of the supramolecular complex resulted in the formation of three geometric isomers of tetracrown-containing dicyclobutano[2.2]metacyclopane, differing in the orientation of the cyclobutane moieties, with the unsymmetrical isomer (>50 %) predominating. The diammonium cations used as the template could be removed after photolysis by simple extraction, and the product was obtained in high yield (82 %). The 1H NMR signals of a mixture of geometric isomers of [2.2]metacyclophane derivative were assigned resorting to quantum chemistry methods (DFT). The kinetic and thermodynamic parameters of thermal isomerization between the endo,endo- and exo,exo-isomers were measured. Tetracrown-containing dicyclobutano[2.2]metacyclophanes are homotetratopic ligands that contain four binding sites for metal and ammonium cations, which is of interest for the design of photo- and thermo-switchable supramolecular devices with a variable complex formation behavior and supramolecular machines owing to the butterfly-type thermal isomerization.</div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100091"},"PeriodicalIF":0.0,"publicationDate":"2024-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000305/pdfft?md5=bbc61009297f58bea762604b4ff7acfe&pid=1-s2.0-S2666951X24000305-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142098210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst (利用多功能微粒铜催化剂对烯酸盐和炔烃进行（半）氢化反应

Tetrahedron chem Pub Date : 2024-08-15 DOI: 10.1016/j.tchem.2024.100089

Samuel Redl, Christoph Topf

{"title":"(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst","authors":"Samuel Redl, Christoph Topf","doi":"10.1016/j.tchem.2024.100089","DOIUrl":"10.1016/j.tchem.2024.100089","url":null,"abstract":"<div>We communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates and alkynes. The introduced protocol is free from any ex ante modifications of the used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligands. The conjugate hydrogenation of enoates and the (selective) reduction of C<img>C bonds is achieved through a [Cu(CH3CN)4]+/tert-butoxide pair whereby we describe a delicate influence of the base cation on the chemoselectivity of the respective transformation. In case of the ester-to-alcohol reduction, a combination of simple CuI and NaOtBu proved to be successful. Deuteration experiments are included to address certain mechanistic aspects of the introduced catalytic system. All requisite chemicals are readily obtainable through commercial channels and the catalyst assembly is set up on the bench without the need for special lab-technical precautions.</div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100089"},"PeriodicalIF":0.0,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000287/pdfft?md5=5437e19b8968da8070a19157b748e4dc&pid=1-s2.0-S2666951X24000287-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142151336","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones 铜催化 1,5-二炔与苯并环丁烯酮的分子间正规 [4 + 1] 环化反应

Tetrahedron chem Pub Date : 2024-08-14 DOI: 10.1016/j.tchem.2024.100090

Jia-Cheng Li , Tian-Qi Hu , Zhou Xu , Bo Zhou , Long-Wu Ye

引用次数: 0

l-Proline catalyzed synthesis of biologically promising heterocycles under sustainable conditions 可持续条件下 l-脯氨酸催化合成具有生物前景的杂环化合物

Tetrahedron chem Pub Date : 2024-08-01 DOI: 10.1016/j.tchem.2024.100087

Rajiv Karmakar , Chhanda Mukhopadhyay

{"title":"l-Proline catalyzed synthesis of biologically promising heterocycles under sustainable conditions","authors":"Rajiv Karmakar , Chhanda Mukhopadhyay","doi":"10.1016/j.tchem.2024.100087","DOIUrl":"10.1016/j.tchem.2024.100087","url":null,"abstract":"<div>Catalysis field wherein a tiny organic molecule like l-proline is an efficient and selectively catalyzed organic reaction. Catalyst-supported organic synthesis is confirmed to be involved in the fast synthesis of novel compounds with selectivity and enhanced biological activities. l-proline catalyzed reactions are valuable tools for the making of different heterocycles, acyclic, and carbocyclic scaffolds that signify the main framework of most of the bio-active compounds. A few decades ago, novel tools for the manufacturing of bio-active molecules had a huge impact on organic chemistry. Subsequently, the synthesis of biologically important heterocycles through a synthetically proficient and environmentally benign route is the important purpose of modern synthetic chemistry. In this review, we discuss only l-proline catalyzed organic reactions (including condensation, addition, asymmetric, multi-components, and other modular reactions) for the sustainable synthesis of biologically promising heterocycles in a single trencher that may provide as a piece of reliable literature for further research in this field.</div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100087"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000263/pdfft?md5=7360970aaabda90d1ad3e7b8516a7217&pid=1-s2.0-S2666951X24000263-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141943434","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Fluoroalcohols for chemical modification of biomolecules 用于生物大分子化学修饰的氟醇

Tetrahedron chem Pub Date : 2024-08-01 DOI: 10.1016/j.tchem.2024.100088

Mohammad Nuruzzaman , Zeinab M. Nizam , Jun Ohata

引用次数: 0

Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions 基本条件下涉及元素硫活化的有机反应的反应活性和机理

Tetrahedron chem Pub Date : 2024-08-01 DOI: 10.1016/j.tchem.2024.100086

Peter Conen , Michael A.R. Meier

引用次数: 0

Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study 8 元氮杂环丁烷的快速合成：综合合成、DFT 和体外研究

Tetrahedron chem Pub Date : 2024-07-17 DOI: 10.1016/j.tchem.2024.100085

Heorhii V. Posternak , Olena D. Semoshkina , Vasyl Y. Hys , Demyd S. Milokhov , Pavlo A. Virych , Svitlana V. Shishkina , Yulian M. Volovenko , Alexey V. Dobrydnev

{"title":"Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study","authors":"Heorhii V. Posternak , Olena D. Semoshkina , Vasyl Y. Hys , Demyd S. Milokhov , Pavlo A. Virych , Svitlana V. Shishkina , Yulian M. Volovenko , Alexey V. Dobrydnev","doi":"10.1016/j.tchem.2024.100085","DOIUrl":"10.1016/j.tchem.2024.100085","url":null,"abstract":"<div>Herein we describe the novel approach to the synthesis of functionalized ind(az)olo-fused 1,2,4-thiadiazocine 1,1-dioxides through the CSIC (Carbanion-mediated Sulfonate (Sulfonamide) Intermolecular Coupling (Intramolecular Cyclization) reaction strategy. 1,2,4-Thiadiazocine 1,1-dioxides (put simply 8-membered azasultams) are increasingly popular but quite underrepresented in the literature compounds, were prepared in two simple steps and good yield from readily available reagents. Particularly, the alkylation of 7-functionalized ind(az)oles with N-(chloromethyl)-N-methylmethanesulfonamide gave the corresponding N-((1H-ind(az)ol-1-yl)methyl)-N-methylmethane-sulfonamides which underwent base-mediated cyclization affording the target 8-membered azasultams. The method worked well and provided azasultams decorated with a set of synthetically valuable handles. The conducted DFT calculations explained and rationalized the experimental data thus allowing us to formulate the rules of the structure‒activity relationship. Despite the prepared compounds showing weak cytotoxicity against the MDA-MB-231 breast cancer cell line, they are considered novel building blocks and perspective pharmacological templates prone to further optimization.</div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100085"},"PeriodicalIF":0.0,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X2400024X/pdfft?md5=8a5acacf07f97bf098fa955907034fa1&pid=1-s2.0-S2666951X2400024X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141728620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Atroposelective total synthesis of strecintide 839 斯特林肽的逆选择全合成 839

Tetrahedron chem Pub Date : 2024-07-10 DOI: 10.1016/j.tchem.2024.100084

Hiroshige Ogawa, Hugh Nakamura

引用次数: 0

Electrochemical oxidations through hypervalent iodine redox catalysis 通过超价碘氧化还原催化实现电化学氧化

Tetrahedron chem Pub Date : 2024-07-05 DOI: 10.1016/j.tchem.2024.100081

Ronit S. Bernard , Ajit Kumar Jha , Marcin Kalek

引用次数: 0

Asymmetric carbohydroxylation of alkenes via sequential photocatalytic oxo-alkylation and enzymatic reduction 通过顺序光催化氧化-烷基化和酶还原实现烯烃的不对称羧羟化反应

Tetrahedron chem Pub Date : 2024-07-04 DOI: 10.1016/j.tchem.2024.100083

Yiyin Liu , Kun Zhu , Xuemei Li , Xiaoyun Wu , Jinhui Feng , Atefeh Roosta , Qiaqing Wu , Dunming Zhu

引用次数: 0