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Transition-Metal-free Michael Addition/Denitrative cyclization of 2′-Nitrochalcones and thioacetamides for the synthesis of thioflavanones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-04 DOI: 10.1016/j.tetlet.2024.155451
Wenjun Wang, Yao Xu, Xiaoming Liao, Zhuoran Yang, Faxiu Feng, Xue Wang, Wenjuan Fan, Xiaoxiang Zhang
{"title":"Transition-Metal-free Michael Addition/Denitrative cyclization of 2′-Nitrochalcones and thioacetamides for the synthesis of thioflavanones","authors":"Wenjun Wang,&nbsp;Yao Xu,&nbsp;Xiaoming Liao,&nbsp;Zhuoran Yang,&nbsp;Faxiu Feng,&nbsp;Xue Wang,&nbsp;Wenjuan Fan,&nbsp;Xiaoxiang Zhang","doi":"10.1016/j.tetlet.2024.155451","DOIUrl":"10.1016/j.tetlet.2024.155451","url":null,"abstract":"<div><div>A novel method for the preparation of thioflavanones from 2′-nitrochalcones and thioacetamides has been developed. The reaction achieved the dissociation of inert groups and employed the thioacetamide as an odorless sulfur source. The desired products were obtained in up to 86% yield under transition-metal-free conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155451"},"PeriodicalIF":1.5,"publicationDate":"2025-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173398","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
I2/p-TSA: An efficient reagent for regioselective synthesis of angularly fused diazabenzocyclo-pentafluorene via iodocyclisation of 11-(arylethynyl)-11H-indeno[1,2-b]quinoxalin-11-ol
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-03 DOI: 10.1016/j.tetlet.2024.155448
Ammundi Jayavel Chirranjeevi Padmashrija , Sathananthan Kannadasan , Ponnusamy Shanmugam
{"title":"I2/p-TSA: An efficient reagent for regioselective synthesis of angularly fused diazabenzocyclo-pentafluorene via iodocyclisation of 11-(arylethynyl)-11H-indeno[1,2-b]quinoxalin-11-ol","authors":"Ammundi Jayavel Chirranjeevi Padmashrija ,&nbsp;Sathananthan Kannadasan ,&nbsp;Ponnusamy Shanmugam","doi":"10.1016/j.tetlet.2024.155448","DOIUrl":"10.1016/j.tetlet.2024.155448","url":null,"abstract":"<div><div>A metal-catalyst-free, efficient, regioselective, electrophilic iodine-<em>p</em>-TSA mediated <em>5-endo-dig</em> cyclization of propargyl alcohol derivative of indenoquinoxalinone for the synthesis of angularly fused diazabenzocyclopentafluorene compounds has been developed. A plausible mechanism mediated by iodine-<em>p</em>-TSA and invoking cyclization via intramolecular nitrogen nucleophiles is provided. The synthetic transformation of products thus obtained was subjected to the following: 1. Dehalogenation, 2. Sonogashira coupling, and 3. Iodine-CAN-mediated oxidation for synthesizing functionalized derivatives of the title compounds was achieved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155448"},"PeriodicalIF":1.5,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143172347","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 diketooximes using radical coupling of 1,3-dicarbonyl compounds and tert-butyl nitrite
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-03 DOI: 10.1016/j.tetlet.2025.155454
Chunxiao Wen, Xiaoshan Zhang, Xingsheng Liu, Ziqiang Zhou, Xuliang Duan
{"title":"Efficient synthesis of diketooximes using radical coupling of 1,3-dicarbonyl compounds and tert-butyl nitrite","authors":"Chunxiao Wen,&nbsp;Xiaoshan Zhang,&nbsp;Xingsheng Liu,&nbsp;Ziqiang Zhou,&nbsp;Xuliang Duan","doi":"10.1016/j.tetlet.2025.155454","DOIUrl":"10.1016/j.tetlet.2025.155454","url":null,"abstract":"<div><div>A novel and efficient nitrosation of 1,3-dicarbonyl compounds with TBN through radical coupling is described. The reactions smoothly led to diketooximes forming up to 99% yield via radical coupling under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155454"},"PeriodicalIF":1.5,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173582","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 a new CTX derivative with naphthalene units
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-03 DOI: 10.1016/j.tetlet.2024.155449
Runnan Chen, Heng Li, Jianmin Jiao, Chen Lin, Leyong Wang
{"title":"Synthesis of a new CTX derivative with naphthalene units","authors":"Runnan Chen,&nbsp;Heng Li,&nbsp;Jianmin Jiao,&nbsp;Chen Lin,&nbsp;Leyong Wang","doi":"10.1016/j.tetlet.2024.155449","DOIUrl":"10.1016/j.tetlet.2024.155449","url":null,"abstract":"<div><div>CTX[P(O)Ph], previously reported by our group, acts as a crystallization chaperone to determine the structures of oily molecules at room temperature. However, its small cavity limits access to guest molecules, emphasizing the need for new analogues with larger cavities. In this study, we report a new analogue of CTX[P(O)Ph], termed (CTH-2-[P(O)Ph]), which has a bigger size of bowl-shaped structure with naphthalene units characterized by its rigidity and completely locked conformation. Crystal of CTH-2-[P(O)Ph] is successfully obtained from a saturated acetonitrile solution. Additionally, we investigated the host–guest behavior of CTH-2-[P(O)Ph] with 1-ethylpyridinium chloride (EPyCl) in acetonitrile.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155449"},"PeriodicalIF":1.5,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173397","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 electron-withdrawing group substituted isatin-N-glycosides by cyclization of formylated aniline-N-glycosides with oxalyl chloride
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-12-28 DOI: 10.1016/j.tetlet.2024.155442
Tanja Stiller, Martin Hein, Peter Langer
{"title":"Synthesis of electron-withdrawing group substituted isatin-N-glycosides by cyclization of formylated aniline-N-glycosides with oxalyl chloride","authors":"Tanja Stiller,&nbsp;Martin Hein,&nbsp;Peter Langer","doi":"10.1016/j.tetlet.2024.155442","DOIUrl":"10.1016/j.tetlet.2024.155442","url":null,"abstract":"<div><div>Electron-withdrawing group substituted isatin-<em>N</em>-glycosides were prepared by cyclization of formylated aniline-<em>N</em>-glycosides with oxalyl chloride. The products were deprotected under mild basic conditions. 2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155442"},"PeriodicalIF":1.5,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173399","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cu-TEMPO catalyzed synthesis of benzo[a]acridines and their photophysical studies
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-12-28 DOI: 10.1016/j.tetlet.2024.155446
Nagarajan Sambavi, Fazlur Rahman Nawaz Khan
{"title":"Cu-TEMPO catalyzed synthesis of benzo[a]acridines and their photophysical studies","authors":"Nagarajan Sambavi,&nbsp;Fazlur Rahman Nawaz Khan","doi":"10.1016/j.tetlet.2024.155446","DOIUrl":"10.1016/j.tetlet.2024.155446","url":null,"abstract":"<div><div>An efficient solvent-free synthesis of benzo[<em>a</em>]acridines <strong>11</strong> was achieved from 2-amino-5-chloro-benzhydrol <strong>8</strong>, 1,2,3,4-tetrahydronaphthalen-2-ol <strong>9</strong>, and benzyl alcohol <strong>10</strong> through Cu-TEMPO catalyzed dehydrogenative Friedlander annulation/C(sp<sup>3</sup>)–H functionalization utilizing DMU-based DESs. A plausible reaction mechanism was proposed based on control experiments and NMR studies. Additionally, the synthesized compounds’ absorption, emission, and synthetic utility studies were evaluated. Further examination revealed compound <strong>11f</strong> exhibits acidochromic properties, resulting in noticeable colour changes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155446"},"PeriodicalIF":1.5,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173584","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
Recent developments on selective homogeneous catalytic transfer hydrogenation of CC using methanol and ethanol
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-12-27 DOI: 10.1016/j.tetlet.2024.155439
Rahul Daga Patil , Sanjay Pratihar
{"title":"Recent developments on selective homogeneous catalytic transfer hydrogenation of CC using methanol and ethanol","authors":"Rahul Daga Patil ,&nbsp;Sanjay Pratihar","doi":"10.1016/j.tetlet.2024.155439","DOIUrl":"10.1016/j.tetlet.2024.155439","url":null,"abstract":"<div><div>This review explores the recent developments in catalytic transfer hydrogenation, focusing on the selective reduction of α,β-unsaturated ketones to saturated ketones, and alkenes to alkanes using methanol and ethanol as sustainable hydrogen sources. Highlighting a range of homogeneous catalysts, including both transition and earth-abundant metals, we provide a comprehensive overview of their role in enhancing reaction efficiency, chemoselectivity, and understanding the mechanism of the catalytic cycle. Specific examples of catalytic systems are discussed, showing their broad substrate tolerance and functional group compatibility. We highlight their growing importance in green chemistry by highlighting the potential of methanol and ethanol as renewable and versatile reagents. It presents insights into future directions for catalyst design and practical applications in industrial processes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155439"},"PeriodicalIF":1.5,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173401","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
Cyclization of sulfoxonium ylides with 2-aminopyridines towards imidazo[1,2-a]pyridines
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-12-26 DOI: 10.1016/j.tetlet.2024.155438
Vu H. Luu , Hoang V.M. Trinh , Dat H. Tran , Tuong Q. Le , Tung T. Nguyen
{"title":"Cyclization of sulfoxonium ylides with 2-aminopyridines towards imidazo[1,2-a]pyridines","authors":"Vu H. Luu ,&nbsp;Hoang V.M. Trinh ,&nbsp;Dat H. Tran ,&nbsp;Tuong Q. Le ,&nbsp;Tung T. Nguyen","doi":"10.1016/j.tetlet.2024.155438","DOIUrl":"10.1016/j.tetlet.2024.155438","url":null,"abstract":"<div><div>A method for cyclization of 2-aminopyridines and sulfoxonium ylides is developed. The approach would avoid the requirement of pre-functionalized, Ortoleva-King typed alpha-haloketones for such cyclization. The annulation was facilitated in the presence of nickel(II) bromide, presumably as the Lewis acid catalyst. An array of functionalities including secondary amine, nitro, and halogen groups were tolerated. Two examples of alkyl sulfoxonium ylides were also presented. Our method feature a new approach to afford synthetically useful <em>C</em>2-substituted imidazo[1,2-<em>a</em>]pyridines from derivatives of benzoic acids.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"156 ","pages":"Article 155438"},"PeriodicalIF":1.5,"publicationDate":"2024-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143173402","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 practical approach for the synthesis of lactate dehydrogenase A inhibitor GNE-140 乳酸脱氢酶A抑制剂GNE-140的合成方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-12-01 DOI: 10.1016/j.tetlet.2024.155395
Jian Zhou , Jiaqi Liang , Qijie Gong , Guowei Zhang , Xiang Li , Xiaojin Zhang , Fulai Yang
{"title":"A practical approach for the synthesis of lactate dehydrogenase A inhibitor GNE-140","authors":"Jian Zhou ,&nbsp;Jiaqi Liang ,&nbsp;Qijie Gong ,&nbsp;Guowei Zhang ,&nbsp;Xiang Li ,&nbsp;Xiaojin Zhang ,&nbsp;Fulai Yang","doi":"10.1016/j.tetlet.2024.155395","DOIUrl":"10.1016/j.tetlet.2024.155395","url":null,"abstract":"<div><div>GNE-140 is the first lactate dehydrogenase A (LDHA) inhibitor that demonstrates both sub-micromolar cellular potency and adequate pharmacokinetic properties, making it suitable for in vivo applications as a tool compound. However, the synthetic route reported by Genentech is complex, relying on transition metal catalysis and yielding low overall amounts. This study presents a practical, scalable method for constructing the core six-membered ring and quaternary carbon center of GNE-140 without transition metal catalysis, achieving a 48.5% racemic yield in a seven-step sequence, paving the way for future LDHA inhibitor development.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155395"},"PeriodicalIF":1.5,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142756991","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
Visible-light-promoted synthesis of alkylated Indolo[2,1-α]isoquinolines using 2‑Mercaptothiazolinium salts as alkyl radical source 以2 -巯基噻唑盐为烷基自由基源，可见光催化合成烷基化吲哚[2,1-α]异喹啉
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-29 DOI: 10.1016/j.tetlet.2024.155397
Chi-Fan Zhu, Fei Li, Jun-Ju Mai, Xiao-Jing Li, Xiasen Dong, Mingyuan Shi, Mei-Hua Shen, Hua-Dong Xu
{"title":"Visible-light-promoted synthesis of alkylated Indolo[2,1-α]isoquinolines using 2‑Mercaptothiazolinium salts as alkyl radical source","authors":"Chi-Fan Zhu,&nbsp;Fei Li,&nbsp;Jun-Ju Mai,&nbsp;Xiao-Jing Li,&nbsp;Xiasen Dong,&nbsp;Mingyuan Shi,&nbsp;Mei-Hua Shen,&nbsp;Hua-Dong Xu","doi":"10.1016/j.tetlet.2024.155397","DOIUrl":"10.1016/j.tetlet.2024.155397","url":null,"abstract":"<div><div>A visible-light-induced radical cascade cyclization of 2-aryl-<em>N</em>-acryloyl indoles with 2‑mercaptothiazolinium salts is reported, furnishing the corresponding indolo[2,1-<em>α</em>]isoquinoline derivatives in good to moderate yields. A series of primary, secondary, and tertiary alkyl bromides were converted conveniently into redox-active thiazolinium salts, which are subsequently transformed into alkyl radicals through interaction with an excited-state photocatalyst. This green and environmentally protocol features broad substrate scope under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155397"},"PeriodicalIF":1.5,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142759718","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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