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An efficient and convenient reaction system based on MnAl layered double oxide for the aerobic oxidation of alkylarenes
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155426
Yihan Shan , Anwei Wang , Sifan Zhang , Deqin Liang , Mingyang He , Weiyou Zhou
{"title":"An efficient and convenient reaction system based on MnAl layered double oxide for the aerobic oxidation of alkylarenes","authors":"Yihan Shan ,&nbsp;Anwei Wang ,&nbsp;Sifan Zhang ,&nbsp;Deqin Liang ,&nbsp;Mingyang He ,&nbsp;Weiyou Zhou","doi":"10.1016/j.tetlet.2024.155426","DOIUrl":"10.1016/j.tetlet.2024.155426","url":null,"abstract":"<div><div>An efficient and convenient catalytic system has been reported for the aerobic oxidation of alkylarenes based on Mn<sub>2</sub>Al layered double oxide (Mn<sub>2</sub>Al-LDO) without any additives. The heterogeneous catalytic system could tolerate various alkylarenes with satisfactory yields. The results demonstrated that Mn species in Mn<sub>2</sub>Al-LDO are the catalytically active sites, and both HAT (hydrogen atom transfer) and ET/PT (electron transfer/proton transfer) processes were suggested to be ascribed for the transformation. A possible reaction mechanism has been proposed based on a series of control experiments.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155426"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159573","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
Dearomative electrophilic spirocyclization via the intramolecular Ritter reaction: Diastereoselective access to hydrogenated spiroindolenines
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155423
Yuliya S. Rozhkova, Arina S. Pegushina, Vyacheslav V. Morozov, Yurii V. Shklyaev
{"title":"Dearomative electrophilic spirocyclization via the intramolecular Ritter reaction: Diastereoselective access to hydrogenated spiroindolenines","authors":"Yuliya S. Rozhkova,&nbsp;Arina S. Pegushina,&nbsp;Vyacheslav V. Morozov,&nbsp;Yurii V. Shklyaev","doi":"10.1016/j.tetlet.2024.155423","DOIUrl":"10.1016/j.tetlet.2024.155423","url":null,"abstract":"<div><div>Dearomative electrophilic spirocyclization based on the intramolecular Ritter reaction of (2-methoxyphenyl)cyclohexan-1-ols with thiocyanates allows the diastereoselective access to the novel hydrogenated spiroindolenines containing a 2,4-cyclohexadienone moiety. The scope and limitations of the reaction were examined. Alkyl thiocyanates and benzyl thiocyanate afforded spiroindolenines in moderate to good yields, whereas the use of <em>β</em>-oxothiocyanates was ineffective. The efficiency of the reaction was also highly dependent on the substitution patterns of the starting alcohols, including substituents on the <em>α</em>-position to the hydroxy group and the 2-methoxyphenyl moiety.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155423"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159578","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
Spotting the unforeseen in the preparation of N-(azetidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155427
Iva Brekalo , Zorica Marušić Ištuk , Milan Mesić , Marijo Čičak , Ivaylo J. Elenkov , Alberto Cuzzolin , Fabio Rancati , Alessandro Accetta
{"title":"Spotting the unforeseen in the preparation of N-(azetidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives","authors":"Iva Brekalo ,&nbsp;Zorica Marušić Ištuk ,&nbsp;Milan Mesić ,&nbsp;Marijo Čičak ,&nbsp;Ivaylo J. Elenkov ,&nbsp;Alberto Cuzzolin ,&nbsp;Fabio Rancati ,&nbsp;Alessandro Accetta","doi":"10.1016/j.tetlet.2024.155427","DOIUrl":"10.1016/j.tetlet.2024.155427","url":null,"abstract":"<div><div>Azetidine derivatives are a popular class of heterocycles in pharmacologically active molecules due to their rigidity, smaller size, and lower lipophilicity compared to pyrrolidines and piperidines, while maintaining similar basicity. However, azetidines exhibit unique reactivity dependent on stereoelectronic factors and reaction conditions, leading to potential instabilities and rearrangements during synthesis. In our attempt to prepare Abrocitinib analogues by replacing the <em>cis</em>-cyclobutane-1,3-diamine scaffold with azetidin-3-amine, we discovered an unforeseen rearrangement of the <em>N</em>-(azetidin-3-yl)-7<em>H</em>-pyrrolo[2,3-<em>d</em>]pyrimidin-4-amine substructure to the tricyclic (2,3-dihydro-1<em>H</em>-imidazo[1,2-<em>c</em>]pyrrolo[3,2-<em>e</em>]pyrimidin-2-yl)methanamine. These findings highlight the need for careful characterization of azetidine-containing compounds when based on <em>N</em>-(azetidin-3-yl)pyrimidin-4-amine substructures and suggest potential methods for preparation of new tricyclic scaffolds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155427"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160320","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 of dihydrooxepinobenzofuranone derivatives via Claisen rearrangement and ring closing metathesis
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155447
Samyuktha Arimalai Dinakararaja , Ethiraj Kannatt Radhakrishnan
{"title":"Synthesis of dihydrooxepinobenzofuranone derivatives via Claisen rearrangement and ring closing metathesis","authors":"Samyuktha Arimalai Dinakararaja ,&nbsp;Ethiraj Kannatt Radhakrishnan","doi":"10.1016/j.tetlet.2024.155447","DOIUrl":"10.1016/j.tetlet.2024.155447","url":null,"abstract":"<div><div>A simple and effective protocol for synthesizing dihydrooxepinobenzofuranone derivatives was developed using Claisen Rearrangement (CR) and Ring Closing Metathesis (RCM). This protocol requires low catalyst loading and moderate heating to construct the 7-membered and 9-membered ring fused aurone derivatives in very short reaction times. Various substrates including biphenyl and hetero aryl aldehydes were well tolerated. The scope and limitations of the reactions were established. The structures of the representative compounds were established by Single Crystal X-ray Diffraction. Similarly, ene–yne RCM products were also synthesized by the same protocol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155447"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159667","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
Reductive heck cyclization and functionalyzation of 5-bromohomoadamant-4-ene carboxamide derivatives: The route to homoadamantene annulated heterocycles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155431
Alexander N. Reznikov, Svetlana Yu. Vostruhina, Yury N. Klimochkin
{"title":"Reductive heck cyclization and functionalyzation of 5-bromohomoadamant-4-ene carboxamide derivatives: The route to homoadamantene annulated heterocycles","authors":"Alexander N. Reznikov,&nbsp;Svetlana Yu. Vostruhina,&nbsp;Yury N. Klimochkin","doi":"10.1016/j.tetlet.2024.155431","DOIUrl":"10.1016/j.tetlet.2024.155431","url":null,"abstract":"<div><div>Palladium catalyzed intramolecular reductive Heck reaction and Heck/cyanation domino sequence of 5-bromohomoadamant-4-ene carboxamides are a convenient synthetic pathway that provides access to polycyclic annulated homoadamanthene derivatives with 5,6-dihydropyridin-2(1<em>H</em>)-one and 1,5-dihydro-2<em>H</em>-pyrrol-2-one cores.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155431"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159669","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
Rearranged and enantiomeric alkaloids from Cephalotaxus sinensis
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155437
Jing Wu , Xin-Yu Liu , Mei-Fen Bao , Bao-Bao Shi , Ming-Xiang Li , Xiang-Hai Cai
{"title":"Rearranged and enantiomeric alkaloids from Cephalotaxus sinensis","authors":"Jing Wu ,&nbsp;Xin-Yu Liu ,&nbsp;Mei-Fen Bao ,&nbsp;Bao-Bao Shi ,&nbsp;Ming-Xiang Li ,&nbsp;Xiang-Hai Cai","doi":"10.1016/j.tetlet.2024.155437","DOIUrl":"10.1016/j.tetlet.2024.155437","url":null,"abstract":"<div><div>Three undescribed alkaloids (<strong>1</strong>–<strong>3</strong>) along with 30 known ones were isolated from the twigs and leaves of <em>Cephalotaxus sinensis</em>. The structures of the new alkaloids were determined through comprehensive spectroscopic analysis and ECD calculations. Cephalosinine A (<strong>1</strong>) with 6/6/6/5 ring system represents a new type of <em>Cephalotaxus</em> alkaloid, which might be formed through a rearrangement from simultaneously isolated cephalotaxinone. Cephalolancine B (<strong>2</strong>) was the second cephalolancine skeleton alkaloid. (+)-Acetylcephalotaxine <em>β</em>-<em>N</em>-oxide (<strong>3</strong>) was an enantiomeric <em>Cephalotaxus</em> alkaloid. The isolated homoerythrina-type alkaloids were evaluated for their <em>in vitro</em> hearing protective effects against neomycin-induced cell death in HEI-OC-1 cells.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155437"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159671","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
Highly diastereoselective total synthesis of Vibegron, a drug for overactive bladder disease
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155429
D.R. Adarsh , T. Ravi Teja , B. Sridhar , B.V. Subba Reddy
{"title":"Highly diastereoselective total synthesis of Vibegron, a drug for overactive bladder disease","authors":"D.R. Adarsh ,&nbsp;T. Ravi Teja ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tetlet.2024.155429","DOIUrl":"10.1016/j.tetlet.2024.155429","url":null,"abstract":"<div><div>A highly efficient and practical approach to the total synthesis of Vibegron, a drug for overactive bladder disease has been achieved <em>through</em> a substrate-directed diastereoselective reduction of ketone to <em>syn-</em>1,2-amino alcohol, enabling the synthesis of Vibegron in a highly stereoselective manner. Another key step involved in this approach is the formation of a <em>cis</em>-pyrrolidine ring <em>via</em> the sequential one-pot Pd/C-catalyzed olefin reduction, debenzylation, Cbz deprotection and reductive amination/cyclization. The total synthesis of Vibegron has been achieved in nine steps with an overall yield of 36 % starting from a readily available <span>d</span>-Serine. It is a non-enzymatic and alternate process to previous approaches.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155429"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160318","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
Asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a thiourea organocatalyst
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155392
Taro Koda , Hiroshi Akutsu , Mitsuaki Suzuki , Kosuke Nakashima , Shin-ichi Hirashima , Akihiro Yoshida , Tsuyoshi Miura , Takashi Yamanoi
{"title":"Asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a thiourea organocatalyst","authors":"Taro Koda ,&nbsp;Hiroshi Akutsu ,&nbsp;Mitsuaki Suzuki ,&nbsp;Kosuke Nakashima ,&nbsp;Shin-ichi Hirashima ,&nbsp;Akihiro Yoshida ,&nbsp;Tsuyoshi Miura ,&nbsp;Takashi Yamanoi","doi":"10.1016/j.tetlet.2024.155392","DOIUrl":"10.1016/j.tetlet.2024.155392","url":null,"abstract":"<div><div>The asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a pyrrolidine–thiourea organocatalyst yielded ε-regioselective addition products in high yields with high enantioselectivities. This work represents the first example of asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155392"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159582","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
An alcohol thioetherification method utilizing a domino dual catalysis strategy
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155433
Zhe Wang , Xinyuan Hu , Chuqiao Song , Honghong Su , Chuanwu Xiong , Guoliang Chen , Xuefei Bao
{"title":"An alcohol thioetherification method utilizing a domino dual catalysis strategy","authors":"Zhe Wang ,&nbsp;Xinyuan Hu ,&nbsp;Chuqiao Song ,&nbsp;Honghong Su ,&nbsp;Chuanwu Xiong ,&nbsp;Guoliang Chen ,&nbsp;Xuefei Bao","doi":"10.1016/j.tetlet.2024.155433","DOIUrl":"10.1016/j.tetlet.2024.155433","url":null,"abstract":"<div><div>Thioethers are prevalent in pharmaceuticals, and its synthetic method utilizing alcohols are receiving more attention due to its environmental benign property. Here, a metal-free dehydrative thioetherification method was reported, enabling the conversion of various alcohols into thioethers via a domino dual catalysis strategy including catalyzed Mitsunobu reaction and followed nucleophilic substitution. Although this method cannot provide satisfactory yields for certain alcohols, it improves the substrate scope of alcohol thioetherification to general primary and secondary alcohols. By employing phosphine oxide and triflic acid as catalysts, 16 phenyl thioethers were synthesized with low to moderate yields via the Dean-Stark distillation. Moreover, the above results indicate that the yield and substrate scope of this method could be enhanced by improving the catalytic rate of the phosphine oxide.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155433"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159585","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
Pd(II)-catalyzed hydroxy group directed synthesis of spiro-fused succinimide isochromenochromenones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155434
Kongkona Gogoi , Bondana Bora , Geetika Borah , Sanjib Gogoi
{"title":"Pd(II)-catalyzed hydroxy group directed synthesis of spiro-fused succinimide isochromenochromenones","authors":"Kongkona Gogoi ,&nbsp;Bondana Bora ,&nbsp;Geetika Borah ,&nbsp;Sanjib Gogoi","doi":"10.1016/j.tetlet.2024.155434","DOIUrl":"10.1016/j.tetlet.2024.155434","url":null,"abstract":"<div><div>A new annulation reaction is developed for the synthesis of isochromene fused chromenones possessing spiro succinimides scaffold. In this hydroxyl group directed Pd(II)-catalyzed reaction, easily affordable 3-hydroxy-2-phenyl-chromenones and maleimides were used as the coupling partners to synthesize a wide range of the biologically relevant spirocyclic compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155434"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160317","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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