A new Lycopodium alkaloid, selactamyuine A (1), isolated from Lycopodium serratum Thunb. var. serratum exhibits a unique C15N2 framework. Selactamyuine A (1) consists of a γ-lactam ring and a decahydroquinoline ring with a slowly rotating N-acetyl group, covalently connected through a methylene linker. Its structure and relative configuration were elucidated based on spectroscopic data and 13C NMR chemical shift calculations, and its absolute configuration was investigated by a combination of CD spectroscopy and TD-DFT calculation.
{"title":"Selactamyuine A, a new C15N2-type Lycopodium alkaloid from Lycopodium serratum Thunb. var. serratum","authors":"Miyuu Sugi , Yusuke Hirasawa , Takefumi Yamashita , Nahoko Uchiyama , Hiroshi Morita","doi":"10.1016/j.tetlet.2025.155894","DOIUrl":"10.1016/j.tetlet.2025.155894","url":null,"abstract":"<div><div>A new <em>Lycopodium</em> alkaloid, selactamyuine A (<strong>1</strong>), isolated from <em>Lycopodium serratum</em> Thunb<em>.</em> var<em>. serratum</em> exhibits a unique C<sub>15</sub>N<sub>2</sub> framework. Selactamyuine A (<strong>1</strong>) consists of a γ-lactam ring and a decahydroquinoline ring with a slowly rotating <em>N</em>-acetyl group, covalently connected through a methylene linker. Its structure and relative configuration were elucidated based on spectroscopic data and <sup>13</sup>C NMR chemical shift calculations, and its absolute configuration was investigated by a combination of CD spectroscopy and TD-DFT calculation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155894"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616049","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}
Pub Date : 2026-02-01Epub Date: 2025-11-21DOI: 10.1016/j.tetlet.2025.155903
Jing Li, Mengyu Gao, Jinyu Zhang
A PhI(OAc)₂-mediated oxidative Joullié-Ugi reaction of amino acids has been developed. This method enables efficient bisamide synthesis via amino acid decarboxylation and subsequent trapping of the iminium intermediate with aryl isocyanides. Conducted in TFE at room temperature, it exhibits a broad scope for isocyanides, delivering products in high yields, as demonstrated on a gram scale.
{"title":"Direct access to cyclic diamides via the oxidative Joullié-Ugi reaction","authors":"Jing Li, Mengyu Gao, Jinyu Zhang","doi":"10.1016/j.tetlet.2025.155903","DOIUrl":"10.1016/j.tetlet.2025.155903","url":null,"abstract":"<div><div>A PhI(OAc)₂-mediated oxidative Joullié-Ugi reaction of amino acids has been developed. This method enables efficient bisamide synthesis via amino acid decarboxylation and subsequent trapping of the iminium intermediate with aryl isocyanides. Conducted in TFE at room temperature, it exhibits a broad scope for isocyanides, delivering products in high yields, as demonstrated on a gram scale.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155903"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145555291","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}
Pub Date : 2026-02-01Epub Date: 2025-12-06DOI: 10.1016/j.tetlet.2025.155923
Bingbing Hou , Shengnan Zhang , Jiajing Su , Fangyi Gong , Wenke Sun , Longjun Ma , Hongxin Liu
Herein, we have developed a novel, environmentally friendly, straightforward, and practical methodology for the construction of 1,3-dihydroxy lactams incorporating multiple quaternary carbon centers through cascade reactions between ketoamides and acetyl compounds in aqueous media. Such molecular architectures are prevalent in natural product systems. This transformation constitutes the first reported instance of employing an amino acid salt to catalyze the formation of dihydroxy lactam-fused polycyclic quaternary carbon frameworks via a sequential aldol and azo-aldol addition cascade process in an aqueous environment. Notably, this reaction exhibits exceptional atom economy, facilitates gram-scale synthesis, and enables multiple catalytic turnovers, delivering the desired products in excellent yields and diastereoselectivities with convenient isolation via centrifugation.
{"title":"Aqueous-phase construction of dihydroxy lactam via cascade reaction catalyzed by amino acid salts","authors":"Bingbing Hou , Shengnan Zhang , Jiajing Su , Fangyi Gong , Wenke Sun , Longjun Ma , Hongxin Liu","doi":"10.1016/j.tetlet.2025.155923","DOIUrl":"10.1016/j.tetlet.2025.155923","url":null,"abstract":"<div><div>Herein, we have developed a novel, environmentally friendly, straightforward, and practical methodology for the construction of 1,3-dihydroxy lactams incorporating multiple quaternary carbon centers through cascade reactions between ketoamides and acetyl compounds in aqueous media. Such molecular architectures are prevalent in natural product systems. This transformation constitutes the first reported instance of employing an amino acid salt to catalyze the formation of dihydroxy lactam-fused polycyclic quaternary carbon frameworks <em>via</em> a sequential aldol and azo-aldol addition cascade process in an aqueous environment. Notably, this reaction exhibits exceptional atom economy, facilitates gram-scale synthesis, and enables multiple catalytic turnovers, delivering the desired products in excellent yields and diastereoselectivities with convenient isolation <em>via</em> centrifugation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155923"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733303","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}
Pub Date : 2026-02-01Epub Date: 2025-11-24DOI: 10.1016/j.tetlet.2025.155908
Meng Yuan , Tian-Rui Lian , Tie-Ying Ding, Yang-Xing Liu, Chao-Shan Da
The polystyrene-supported N-prolyl tetrapeptide was disclosed to catalyze the asymmetric addition of aldehydes to nitroolefins with water as solvent, achieving high yields, good enantioselectivities, and excellent diastereoselectivities. The heterogeneous catalyst can be successfully recovered and reused at least five times without loss of stereoselectivity. The results demonstrated that the configuration of the Michael adduct depends on both the configuration of the N-terminal amino acid and whether the N-terminal residue is a prolyl residue or a primary amino acid. The secondary structure of the catalyst is also seriously responsible for the direction of the asymmetric induction.
{"title":"Polystyrene-supported N-prolyl tetrapeptides catalyzed asymmetric Michael addition of aldehydes to nitroolefins","authors":"Meng Yuan , Tian-Rui Lian , Tie-Ying Ding, Yang-Xing Liu, Chao-Shan Da","doi":"10.1016/j.tetlet.2025.155908","DOIUrl":"10.1016/j.tetlet.2025.155908","url":null,"abstract":"<div><div>The polystyrene-supported <em>N</em>-prolyl tetrapeptide was disclosed to catalyze the asymmetric addition of aldehydes to nitroolefins with water as solvent, achieving high yields, good enantioselectivities, and excellent diastereoselectivities. The heterogeneous catalyst can be successfully recovered and reused at least five times without loss of stereoselectivity. The results demonstrated that the configuration of the Michael adduct depends on both the configuration of the <em>N</em>-terminal amino acid and whether the <em>N</em>-terminal residue is a prolyl residue or a primary amino acid. The secondary structure of the catalyst is also seriously responsible for the direction of the asymmetric induction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155908"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616503","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}
Pub Date : 2026-01-15Epub Date: 2025-10-18DOI: 10.1016/j.tetlet.2025.155863
James Mersch , Yehenew Agazie , Michael A. Menze , Mary E. Konkle , Jason D. Huber , Werner J. Geldenhuys
MitoNEET (CISD1), an [2Fe-2S] cluster protein located on the outer mitochondrial membrane and known for its role in cellular redox regulation and bioenergetics, has been identified as a novel ferroptosis-related drug target in neurodegeneration and cancer. The mitoNEET ligand NEET ligand-1 (NL-1) was developed as a pharmacological tool to elucidate the biochemistry of the novel protein in a variety of disease states, ranging from oncology to neurodegenerative disorders. Here, we present a scalable gram-level synthesis of the thiazolidinedione (TZD) containing NL-1 from the precursor CI-987 using the Hantzsch ester reduction as an alternative to conventional lithium borohydride or cobalt chloride-based methods. This optimized protocol enables the reliable production of NL-1 in quantities sufficient for preclinical disease modeling.
{"title":"Gram-scale synthesis of the thiazolidinedione-based mitoNEET ligand NL-1 using a Hantzsch ester reduction","authors":"James Mersch , Yehenew Agazie , Michael A. Menze , Mary E. Konkle , Jason D. Huber , Werner J. Geldenhuys","doi":"10.1016/j.tetlet.2025.155863","DOIUrl":"10.1016/j.tetlet.2025.155863","url":null,"abstract":"<div><div>MitoNEET (CISD1), an [2Fe-2S] cluster protein located on the outer mitochondrial membrane and known for its role in cellular redox regulation and bioenergetics, has been identified as a novel ferroptosis-related drug target in neurodegeneration and cancer. The mitoNEET ligand NEET ligand-1 (NL-1) was developed as a pharmacological tool to elucidate the biochemistry of the novel protein in a variety of disease states, ranging from oncology to neurodegenerative disorders. Here, we present a scalable gram-level synthesis of the thiazolidinedione (TZD) containing NL-1 from the precursor CI-987 using the Hantzsch ester reduction as an alternative to conventional lithium borohydride or cobalt chloride-based methods. This optimized protocol enables the reliable production of NL-1 in quantities sufficient for preclinical disease modeling.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155863"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361383","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}
Novel chiral organocatalysts (3a-e), in which both pyridine N-oxide and urea functional groups are bonded to a chiral aminoindanol scaffold, were designed for the enantioselective hydrosilylation of imines using HSiCl3. The reactions of the imines with HSiCl3 in the presence of the bifunctional organocatalysts proceeded effectively, and the corresponding chiral amines were obtained with up to 98 % ee using only 0.1 mol% catalyst loading of 3e.
{"title":"Enantioselective reductive hydrosilylation of imines using HSiCl3 with a trace of bifunctional chiral pyridine N-oxide organocatalyst bearing a urea hydrogen-bond donor","authors":"Gakushi Morita, Hinoki Sakamura, Yusuke Fukushima, Michimasa Hayashi, Tetsuya Fujimoto","doi":"10.1016/j.tetlet.2025.155901","DOIUrl":"10.1016/j.tetlet.2025.155901","url":null,"abstract":"<div><div>Novel chiral organocatalysts (<strong>3a-e</strong>), in which both pyridine <em>N</em>-oxide and urea functional groups are bonded to a chiral aminoindanol scaffold, were designed for the enantioselective hydrosilylation of imines using HSiCl<sub>3</sub>. The reactions of the imines with HSiCl<sub>3</sub> in the presence of the bifunctional organocatalysts proceeded effectively, and the corresponding chiral amines were obtained with up to 98 % ee using only 0.1 mol% catalyst loading of <strong>3e</strong>.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155901"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576483","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}
Pub Date : 2026-01-15Epub Date: 2025-10-28DOI: 10.1016/j.tetlet.2025.155851
Maduabuchi Angus Modum , Stefan Smulik , James W. Kim , Andrea Gorrell , Kalindi D. Morgan
Transformation of L-sorbose via sequential acetonide protection, oxidation, and lactonization is a pivotal route towards vitamin C synthesis, yet traditional batch and large fermentation processes have not been radically re-imagined in decades. Herein, we report a step-wise flow platform that accomplishes three key transformations of L-sorbose in minutes with high yields and minimal purification. In the first module, L-sorbose undergoes diacetonide protection in a PTFE coil reactor at 0–5 °C, reaching 95 % (crude) conversion in 30 min. The protected sugar is then oxidized inline to the corresponding 2-keto-L-gluconic acid with final direct lactonization to l-ascorbic acid. Thus, under current conditions, the total conversion of L-sorbose to Vitamin C is achieved in 90 total minutes with 85 % crude Vitamin C yield and 57 % pure Vitamin C yield.
l -山梨糖通过连续的丙酮保护、氧化和内酯化转化是合成维生素C的关键途径，但传统的批量和大型发酵过程在几十年来没有从根本上重新设想。在此，我们报告了一个逐步流动平台，在几分钟内以高产量和最少的纯化完成l -山梨糖的三个关键转化。在第一个模块中，L-sorbose在0-5°C的聚四氟乙烯盘管反应器中接受二丙酮保护，在30分钟内达到95%（粗）转化率。然后，受保护的糖被氧化成相应的2-酮- l-葡萄糖酸，最后直接内酯化成l-抗坏血酸。因此，在目前的条件下，l -山梨糖到维生素C的总转化在90分钟内实现，粗维生素C收率为85%，纯维生素C收率为57%。
{"title":"Step-wise flow synthesis of l-ascorbic acid from L-sorbose","authors":"Maduabuchi Angus Modum , Stefan Smulik , James W. Kim , Andrea Gorrell , Kalindi D. Morgan","doi":"10.1016/j.tetlet.2025.155851","DOIUrl":"10.1016/j.tetlet.2025.155851","url":null,"abstract":"<div><div>Transformation of L-sorbose via sequential acetonide protection, oxidation, and lactonization is a pivotal route towards vitamin C synthesis, yet traditional batch and large fermentation processes have not been radically re-imagined in decades. Herein, we report a step-wise flow platform that accomplishes three key transformations of L-sorbose in minutes with high yields and minimal purification. In the first module, L-sorbose undergoes diacetonide protection in a PTFE coil reactor at 0–5 °C, reaching 95 % (crude) conversion in 30 min. The protected sugar is then oxidized inline to the corresponding 2-keto-L-gluconic acid with final direct lactonization to <span>l</span>-ascorbic acid. Thus, under current conditions, the total conversion of L-sorbose to Vitamin C is achieved in 90 total minutes with 85 % crude Vitamin C yield and 57 % pure Vitamin C yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155851"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145414308","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}
Pub Date : 2026-01-15Epub Date: 2025-10-25DOI: 10.1016/j.tetlet.2025.155873
Guiqin Yu , Xuming Liu , Yan Ming , Bei Wang, Xiang Liu
A novel benzindole-based donor–acceptor–donor (D–A–D) fluorescent probe (HST) has been rationally designed and synthesized for the highly selective and sensitive detection of hydrazine (N₂H₄). The sensing mechanism is based on the hydrazine-triggered nucleophilic addition to the conjugated double bond, which disrupts the intramolecular charge transfer (ICT) process, resulting in significant fluorescence quenching. HST demonstrates remarkable features including a large Stokes shift (136 nm), rapid response within 3 min, excellent selectivity, and a low detection limit (3.47 μM). Furthermore, HST enables direct, naked-eye recognition of hydrazine under both visible and UV light. These findings suggest HST as a promising tool for practical applications in environmental and biological hydrazine monitoring.
{"title":"Benzindole-based donor-acceptor-donor ratiometric-type fluorescent probe for hydrazine","authors":"Guiqin Yu , Xuming Liu , Yan Ming , Bei Wang, Xiang Liu","doi":"10.1016/j.tetlet.2025.155873","DOIUrl":"10.1016/j.tetlet.2025.155873","url":null,"abstract":"<div><div>A novel benzindole-based donor–acceptor–donor (D–A–D) fluorescent probe (HST) has been rationally designed and synthesized for the highly selective and sensitive detection of hydrazine (N₂H₄). The sensing mechanism is based on the hydrazine-triggered nucleophilic addition to the conjugated double bond, which disrupts the intramolecular charge transfer (ICT) process, resulting in significant fluorescence quenching. HST demonstrates remarkable features including a large Stokes shift (136 nm), rapid response within 3 min, excellent selectivity, and a low detection limit (3.47 μM). Furthermore, HST enables direct, naked-eye recognition of hydrazine under both visible and UV light. These findings suggest HST as a promising tool for practical applications in environmental and biological hydrazine monitoring.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155873"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361388","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}
Pub Date : 2026-01-15Epub Date: 2025-10-21DOI: 10.1016/j.tetlet.2025.155869
Sai Zhao , Lijuan Zhu , Nian Tong , Qi Qi
A novel synthetic route has been developed for the preparation of a key drug impurity of alectinib, a highly potent ALK inhibitor used in the treatment of non-small cell lung cancer. This impurity, designated as compound 1 and chemically identified as 9-ethyl-6,6-dimethyl-8-[4-(1,4-oxazinan-4-yl)hexahydropyridin-1-yl]-11-oxo-6,11-dihydrobenzo[d]naphtho[3,2-b]furan-3‑carbonitrile, originates from the initial cyclization step in the synthetic procedure of alectinib. In comparison to the method described in the patent, the new route offers several advantages, including higher yields, reduced Pd catalyst loading, and enhanced sustainability. This approach is expected to contribute significantly to the advancement of process chemistry and to improved quality control in the manufacture of alectinib.
{"title":"A novel synthetic route to a process-related impurity of alectinib","authors":"Sai Zhao , Lijuan Zhu , Nian Tong , Qi Qi","doi":"10.1016/j.tetlet.2025.155869","DOIUrl":"10.1016/j.tetlet.2025.155869","url":null,"abstract":"<div><div>A novel synthetic route has been developed for the preparation of a key drug impurity of alectinib, a highly potent ALK inhibitor used in the treatment of non-small cell lung cancer. This impurity, designated as compound <strong>1</strong> and chemically identified as 9-ethyl-6,6-dimethyl-8-[4-(1,4-oxazinan-4-yl)hexahydropyridin-1-yl]-11-oxo-6,11-dihydrobenzo[<em>d</em>]naphtho[3,2-b]furan-3‑carbonitrile, originates from the initial cyclization step in the synthetic procedure of alectinib. In comparison to the method described in the patent, the new route offers several advantages, including higher yields, reduced Pd catalyst loading, and enhanced sustainability. This approach is expected to contribute significantly to the advancement of process chemistry and to improved quality control in the manufacture of alectinib.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155869"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145414307","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}
A concise and efficient one-pot two-step sequential synthesis of sulfonyl azides from readily available thiols has been developed. This method involves an initial reaction of the thiol with TCCA in 96 % ethanol to generate the corresponding sulfonyl chloride. Subsequently, an aqueous solution of sodium azide is added to the reaction mixture, leading to the formation of the desired sulfonyl azide. Utilizing TCCA as a dual oxidant and chlorinating agent, this novel approach enables the direct conversion of thiols to sulfonyl azides in good to high yields (70–93 %) at room temperature. This streamlined approach provides facile access to a diverse array of sulfonyl azide derivatives.
{"title":"Direct synthesis of sulfonyl azides from thiols and sodium azide: a one-pot sequential approach utilizing TCCA as an oxidizing and chlorinating agent","authors":"Fateh Golmoradi , Masoumeh Foroutan Koudehi , Hossein Fasihi Dastjerdi , Farzad Nikpour , Ramin Zibaseresht","doi":"10.1016/j.tetlet.2025.155897","DOIUrl":"10.1016/j.tetlet.2025.155897","url":null,"abstract":"<div><div>A concise and efficient one-pot two-step sequential synthesis of sulfonyl azides from readily available thiols has been developed. This method involves an initial reaction of the thiol with TCCA in 96 % ethanol to generate the corresponding sulfonyl chloride. Subsequently, an aqueous solution of sodium azide is added to the reaction mixture, leading to the formation of the desired sulfonyl azide. Utilizing TCCA as a dual oxidant and chlorinating agent, this novel approach enables the direct conversion of thiols to sulfonyl azides in good to high yields (70–93 %) at room temperature. This streamlined approach provides facile access to a diverse array of sulfonyl azide derivatives.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155897"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576485","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}
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