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Ring-opening ring-closing strategy towards construction of aza-heterocycles from aziridines 叠氮杂环的开环合环构造策略
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-04-01 Epub Date: 2026-01-15 DOI: 10.1016/j.tetlet.2026.155960
Surabhi Upadhyay , Smriti Suryavanshi , Ambika Asati , Manorama Singh , Ankita Rai , Vijai K. Rai
{"title":"Ring-opening ring-closing strategy towards construction of aza-heterocycles from aziridines","authors":"Surabhi Upadhyay ,&nbsp;Smriti Suryavanshi ,&nbsp;Ambika Asati ,&nbsp;Manorama Singh ,&nbsp;Ankita Rai ,&nbsp;Vijai K. Rai","doi":"10.1016/j.tetlet.2026.155960","DOIUrl":"10.1016/j.tetlet.2026.155960","url":null,"abstract":"<div><div>Recent advances in the ring-opening and ring-closing transformations of the three-membered aza-heterocycle aziridine have garnered significant attention in heterocyclic chemistry. Due to their highly strained structure, aziridines readily undergo nucleophilic ring-opening reactions, typically involving cleavage of the C–N bond, followed by cyclization or cycloaddition processes. These transformations enable access to a diverse array of four- to seven-membered heterocycles (often containing one to three heteroatoms), many of which possess structural features of biological and medicinal importance. In this context, the past decade (2015–2025) has seen the emergence of numerous simple, efficient, and sustainable strategies for the synthesis, reactivity, and synthetic utility of aziridines. These developments are comprehensively summarized in this review.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155960"},"PeriodicalIF":1.5,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025486","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
Microwave reactor assisted chiral Brønsted acid catalyzed asymmetric synthesis 微波反应器辅助手性Brønsted酸催化不对称合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-04-01 Epub Date: 2026-01-20 DOI: 10.1016/j.tetlet.2026.155976
Jesscia E. Carsley, Mason T. Gates, Kimberly S. Petersen
{"title":"Microwave reactor assisted chiral Brønsted acid catalyzed asymmetric synthesis","authors":"Jesscia E. Carsley,&nbsp;Mason T. Gates,&nbsp;Kimberly S. Petersen","doi":"10.1016/j.tetlet.2026.155976","DOIUrl":"10.1016/j.tetlet.2026.155976","url":null,"abstract":"<div><div>Microwave reactors have been used in organic synthesis to facilitate reactions since the 1980s. In this paper we show that the reaction time can be substantially shortened for our previously developed chiral Brønsted acid catalyzed desymmetrization of diesters to yield lactones when performed in the microwave from 72 h to 20 min without loss in yield or enantiopurity. Three additional organocatalyzed asymmetric reactions from current literature were explored and shown to exhibit similar benefits with the use of a microwave reactor. Although not traditionally thought of as a tool in asymmetric organocatalysis, we show that microwave reactors can benefit many enantioselective reactions, particularly those with long reaction times.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155976"},"PeriodicalIF":1.5,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025507","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-induced direct synthesis of indolizine derivatives via radical cyclization of 3-cyano-1,4-dihydropyridine compounds 可见光诱导下3-氰基-1,4-二氢吡啶化合物自由基环化直接合成吲哚嗪衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-16 DOI: 10.1016/j.tetlet.2025.155933
Guiyun Tang , Kai Li , Xingdan Wang , Shuo Mu , Yuanming Lv , Qidi Zhong , Huanhuan Jiang , Zhiqiang Xie
{"title":"Visible-light-induced direct synthesis of indolizine derivatives via radical cyclization of 3-cyano-1,4-dihydropyridine compounds","authors":"Guiyun Tang ,&nbsp;Kai Li ,&nbsp;Xingdan Wang ,&nbsp;Shuo Mu ,&nbsp;Yuanming Lv ,&nbsp;Qidi Zhong ,&nbsp;Huanhuan Jiang ,&nbsp;Zhiqiang Xie","doi":"10.1016/j.tetlet.2025.155933","DOIUrl":"10.1016/j.tetlet.2025.155933","url":null,"abstract":"<div><div>Herein, we describe a visible-light-induced, TEMPO-mediated radical cyclization strategy for the efficient synthesis of indolizine derivatives from 3-cyano-1,4-dihydropyridine substrates. This metal- and base-free protocol proceeds under ambient conditions, affording the target products in good yields with broad functional group tolerance. The method features a simple setup, low energy consumption, and mild reaction conditions, offering a practical and environmentally benign route to access this important class of indolizine derivatives.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155933"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145789150","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
Thiophosphonothioates from oxiranes 硫代膦硫代化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-19 DOI: 10.1016/j.tetlet.2025.155943
Ian P. Shire, Zarko Boskovic
{"title":"Thiophosphonothioates from oxiranes","authors":"Ian P. Shire,&nbsp;Zarko Boskovic","doi":"10.1016/j.tetlet.2025.155943","DOIUrl":"10.1016/j.tetlet.2025.155943","url":null,"abstract":"<div><div>Heating oxiranes with Lawesson's reagent in aromatic solvents results in the formation of thiophosphonothioates. The reaction proceeds most efficiently with substrates where elimination is hindered by their geometry. The observed regioselectivity can be explained by cation stabilization in bicyclic systems. In particular, electron-donating groups significantly enhance the stabilization of carbocations at the homobenzylic position in rigid bicyclic frameworks.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155943"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837873","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
The structure-property correlation in homocoupling reaction; a case study by clamshell and planar palladium complexes 均偶联反应的构效关系翻盖壳和平面钯配合物的案例研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-27 DOI: 10.1016/j.tetlet.2025.155955
Hassan Izadi , Alireza Abbasi , Ali Nemati Kharat , Hamid Reza Khavasi
{"title":"The structure-property correlation in homocoupling reaction; a case study by clamshell and planar palladium complexes","authors":"Hassan Izadi ,&nbsp;Alireza Abbasi ,&nbsp;Ali Nemati Kharat ,&nbsp;Hamid Reza Khavasi","doi":"10.1016/j.tetlet.2025.155955","DOIUrl":"10.1016/j.tetlet.2025.155955","url":null,"abstract":"<div><div>In the present paper, Ullmann homocoupling reaction of bromobenzene derivatives by using various palladium complexes is chosen for the investigation of correlation between structure and properties. In this regard, novel palladium complexes with a series of para-substituted amidate ligands, N-(aryl)pyrazine-2-carboxamide, (aryl = 4-ethylphenyl, 4-nitrophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 4-iodophenyl and 4-hydroxyphenyl are synthesized and structurally characterized. The experimental results prove that there is a linear correlation between the electron-withdrawing and -donating properties of the substituents and the catalytic activity. Furthermore, the clamshell or planar coordination geometry around the Pd center, exhibits a vital impact on the catalytic activity of the complexes. Our results show that among these various Pd(II) compounds, complex including methoxy substituent ligand displayed significant activity in Ullmann homocoupling reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155955"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881187","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
Non-symmetrical Bisphosphonated allylic amines: unprecedented synthesis from α-aminomonophosphonates 非对称双膦化烯丙基胺：前所未有的α-氨基单膦酸盐合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-19 DOI: 10.1016/j.tetlet.2025.155932
Ichrak Souii , Momtez Jmaï , Jesús M. de los Santos , Hédi M'Rabet
{"title":"Non-symmetrical Bisphosphonated allylic amines: unprecedented synthesis from α-aminomonophosphonates","authors":"Ichrak Souii ,&nbsp;Momtez Jmaï ,&nbsp;Jesús M. de los Santos ,&nbsp;Hédi M'Rabet","doi":"10.1016/j.tetlet.2025.155932","DOIUrl":"10.1016/j.tetlet.2025.155932","url":null,"abstract":"<div><div>Interest in the synthetic routes to aminobisphosphonates has been steadily increasing due to their wide range of applications. In this work, we report a novel approach for the preparation of two series of non-symmetric allylic aminobisphosphonates under mild reaction conditions. The target compounds were obtained via nucleophilic substitution of α-aminophosphonates with two different phosphonated bromine derivatives: 2-bromoethyl diethyl phosphonate and ethyl 2-(bromomethyl)-3-(diethoxyphosphoryl)acrylate. In the case of <em>N</em>-(phosphorylmethyl)-<em>N</em>-(2-phosphorylethyl) allylamines, the allyl fragment originates from allyl-substituted α-aminophosphonates, whereas for <em>N</em>-(phosphorylmethyl)-3-phosphorylallylamine, it is introduced through the ethyl 2-(bromomethyl)-3-(diethoxyphosphoryl)acrylate synthon.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155932"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145789149","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
Ent-labdane diterpenoids including a rare 3,19-dinor-ent-labdane from Caesalpinia decapetala Alston 对戊二萜，包括一种稀有的3,19对戊二萜
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-16 DOI: 10.1016/j.tetlet.2025.155930
Yongchun Gao , Xi Yang , Liqin Wang
{"title":"Ent-labdane diterpenoids including a rare 3,19-dinor-ent-labdane from Caesalpinia decapetala Alston","authors":"Yongchun Gao ,&nbsp;Xi Yang ,&nbsp;Liqin Wang","doi":"10.1016/j.tetlet.2025.155930","DOIUrl":"10.1016/j.tetlet.2025.155930","url":null,"abstract":"<div><div>Four undescribed <em>ent</em>-labdane diterpenes, caesldecapins A–D (<strong>1–4</strong>), along with four artificial or known <em>ent</em>-labdane diterpenes (<strong>5</strong>–<strong>8</strong>) were isolated from the twigs and leaves of <em>Caesalpinia decapetala.</em> Their structures were elucidated by extensive spectroscopic analyses, including HRMS, 1D and 2D NMR spectral data. Caesldecapin D (<strong>4</strong>) was a rare 2,3:3,4-diseco-3,19-dinor-<em>ent</em>-labdane diterpene.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155930"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145789152","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
Ruthenium(II)-catalyzed 1,3,5-triazine group directed CH amidation of anilines with dioxazolones 钌（II）催化1,3,5-三嗪基团导向苯胺与二恶唑酮的CH酰胺化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-27 DOI: 10.1016/j.tetlet.2025.155956
Fuzhong Han , Li Shi , Lina Jia , Xiangping Hu
{"title":"Ruthenium(II)-catalyzed 1,3,5-triazine group directed CH amidation of anilines with dioxazolones","authors":"Fuzhong Han ,&nbsp;Li Shi ,&nbsp;Lina Jia ,&nbsp;Xiangping Hu","doi":"10.1016/j.tetlet.2025.155956","DOIUrl":"10.1016/j.tetlet.2025.155956","url":null,"abstract":"<div><div>An efficient Ru(II)-catalyzed 1,3,5-triazine group directed C<img>H amidation protocol for anilines has been developed by employing dioxazolones as an amidating reagent. This protocol demonstrated remarkable substrate scope, smoothly converting a wide range of 1,3,5-triazine-fused aniline derivatives and diversely substituted dioxazolones variants into the corresponding products in good to excellent yields with good site selectivity and functional group tolerance. The reaction mechanism was performed using deuteration studies and control experiments, providing insights into the catalytic cycle.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155956"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881188","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 regioselective alkylation of 2-aryl-1,2,3-triazoles with maleimides through ortho-CH functionalization 2-芳基-1,2,3-三唑与马来酰亚胺的高区域选择性烷基化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-18 DOI: 10.1016/j.tetlet.2025.155936
P. Krishna Rao , T. Gowthami , P. Narayana Reddy , B. Sridhar , B.V. Subba Reddy , P. Padmaja
{"title":"Highly regioselective alkylation of 2-aryl-1,2,3-triazoles with maleimides through ortho-CH functionalization","authors":"P. Krishna Rao ,&nbsp;T. Gowthami ,&nbsp;P. Narayana Reddy ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy ,&nbsp;P. Padmaja","doi":"10.1016/j.tetlet.2025.155936","DOIUrl":"10.1016/j.tetlet.2025.155936","url":null,"abstract":"<div><div>We established a strategy for triazole directed, rhodium-catalyzed regio-<em>ortho</em>-selective C<img>H alkylation of 2-aryl-1,2,3-triazoles with maleimides. This transformation provided a straightforward approach for the synthesis of biologically important succinimide-triazole hybrid molecules in moderate to good yields with good functional group compatibility. This method avoids the tedious pre-synthesis of 2-aryl-1,2,3-triazole <em>N</em>-oxide precursor.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155936"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881190","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
Pincer manganese-catalyzed dehydrogenative synthesis of thiophene carboxylic acids from thiophene alcohols and aldehydes 钳子锰催化噻吩醇和醛脱氢合成噻吩羧酸
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-03-01 Epub Date: 2025-12-23 DOI: 10.1016/j.tetlet.2025.155950
Shan Lv , Hongxiang Tan , Xiaohui Jia , Yuntao Fan , Siyi Song , Feng He , Tianshu Kou , Zhihui Shao
{"title":"Pincer manganese-catalyzed dehydrogenative synthesis of thiophene carboxylic acids from thiophene alcohols and aldehydes","authors":"Shan Lv ,&nbsp;Hongxiang Tan ,&nbsp;Xiaohui Jia ,&nbsp;Yuntao Fan ,&nbsp;Siyi Song ,&nbsp;Feng He ,&nbsp;Tianshu Kou ,&nbsp;Zhihui Shao","doi":"10.1016/j.tetlet.2025.155950","DOIUrl":"10.1016/j.tetlet.2025.155950","url":null,"abstract":"<div><div>Thiophene carboxylic acids are pivotal building blocks in medicinal and material chemistry. However, their synthesis relies on traditional stoichiometric oxidants or precious-metal catalysts, which are environmentally and economically concerning. This study reported a sustainable and atom-economical method for directly synthesizing thiophenic carboxylic acids using a manganese-catalyzed dehydrogenative coupling. A well-defined pincer Mn(I) complex as the catalyst was utilized to smoothly convert a wide range of thiophene alcohols and thiophene aldehydes to the corresponding carboxylic acids with the liberation of H<sub>2</sub> as the sole byproduct. The protocol exhibited excellent functional group tolerance and high efficiency. Additionally, the bifunctional thiophene alcohols or thiophene aldehydes could be efficiently converted into dicarboxylic acid products under optimal reaction conditions. This study provided a green and practical alternative to the existing methodologies.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155950"},"PeriodicalIF":1.5,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922014","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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