Pub Date : 2025-11-21DOI: 10.1016/j.tetlet.2025.155899
Jiting Song , Xianheng Wang , Mingyun Liu , Changkuo Zhao
A series of novel spirooxindole quinazolones were designed and synthesized in high yields by a two-step procedure from substituted evodiamine derivatives. The structure of obtained target compounds were identified by 1H NMR, 13C NMR, HRMS and X-ray spectrum.
{"title":"Skleton rearrangement to prepare spirooxindolequinazolone","authors":"Jiting Song , Xianheng Wang , Mingyun Liu , Changkuo Zhao","doi":"10.1016/j.tetlet.2025.155899","DOIUrl":"10.1016/j.tetlet.2025.155899","url":null,"abstract":"<div><div>A series of novel spirooxindole quinazolones were designed and synthesized in high yields by a two-step procedure from substituted evodiamine derivatives. The structure of obtained target compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR, HRMS and X-ray spectrum.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155899"},"PeriodicalIF":1.5,"publicationDate":"2025-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145555290","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 : 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":"2025-11-21","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 : 2025-11-20DOI: 10.1016/j.tetlet.2025.155902
K.E. Wier, S.M. Conner, R.F. Berger, G.W. O'Neil
Two 3-fluorosilinanes featuring different substitution at silicon were synthesized and their conformations analyzed by NMR and DFT. Based on the results, both compounds prefer a conformation wherein the fluorine atom is oriented equatorial rather than axial, which would have placed the partially negative fluorine (Fδ-) closer in space to partially positive silicon (Siδ+). Therefore, the conformational preference of these systems is thought to be controlled primarily by sterics as well as hyperconjugative stabilization (σC-Si → σ*C-F).
合成了两个在硅上具有不同取代的3-氟硅烷，并用NMR和DFT分析了它们的构象。根据结果，这两种化合物都倾向于氟原子取向赤道而不是轴向的构象，这将使部分负的氟（Fδ-）在空间上更靠近部分正的硅（Siδ+）。因此，这些体系的构象偏好主要是由立体构型和超共轭稳定（σ c - si→σ*C-F）控制的。
{"title":"Examining the silicon‑fluorine gauche effect in 3-fluoro silacyclohexanes","authors":"K.E. Wier, S.M. Conner, R.F. Berger, G.W. O'Neil","doi":"10.1016/j.tetlet.2025.155902","DOIUrl":"10.1016/j.tetlet.2025.155902","url":null,"abstract":"<div><div>Two 3-fluorosilinanes featuring different substitution at silicon were synthesized and their conformations analyzed by NMR and DFT. Based on the results, both compounds prefer a conformation wherein the fluorine atom is oriented equatorial rather than axial, which would have placed the partially negative fluorine (F<sup>δ-</sup>) closer in space to partially positive silicon (Si<sup>δ+</sup>). Therefore, the conformational preference of these systems is thought to be controlled primarily by sterics as well as hyperconjugative stabilization (σ<sub>C-Si</sub> → σ*<sub>C-F</sub>).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155902"},"PeriodicalIF":1.5,"publicationDate":"2025-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576484","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 : 2025-11-19DOI: 10.1016/j.tetlet.2025.155904
Yuliya S. Rozhkova, Arina S. Pegushina, Vyacheslav V. Morozov, Daria V. Eroshenko, Yurii V. Shklyaev
A novel acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic and heteroaromatic ortho-aminonitriles was developed, resulting in the diastereoselective formation of new polycyclic acridines and related heterocycles, including partially hydrogenated quinolino[4,3,2-kl]acridines, cyclopenta[5,6]pyrido[4,3,2-kl]acridine, and fused pyrido[4,3,2-gh]phenanthridines, in 14–81 % yields. The developed domino sequence involves initial dearomative electrophilic ortho-spirocyclization via the Ritter reaction, followed by intramolecular nucleophilic trapping of the spiro-σ-intermediate by the amino group and subsequent aromatization via [1,2]-alkyl shift. Several of the synthesized quinolino[4,3,2-kl]acridines showed high antibacterial activity against S. epidermidis ATCC 29887 and M. smegmatis mc2 155.
{"title":"Acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic/heteroaromatic ortho-aminonitriles: Diastereoselective access to polycyclic acridines and related heterocycles","authors":"Yuliya S. Rozhkova, Arina S. Pegushina, Vyacheslav V. Morozov, Daria V. Eroshenko, Yurii V. Shklyaev","doi":"10.1016/j.tetlet.2025.155904","DOIUrl":"10.1016/j.tetlet.2025.155904","url":null,"abstract":"<div><div>A novel acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic and heteroaromatic <em>ortho</em>-aminonitriles was developed, resulting in the diastereoselective formation of new polycyclic acridines and related heterocycles, including partially hydrogenated quinolino[4,3,2-<em>kl</em>]acridines, cyclopenta[5,6]pyrido[4,3,2-<em>kl</em>]acridine, and fused pyrido[4,3,2-<em>gh</em>]phenanthridines, in 14–81 % yields. The developed domino sequence involves initial dearomative electrophilic <em>ortho</em>-spirocyclization <em>via</em> the Ritter reaction, followed by intramolecular nucleophilic trapping of the spiro-<em>σ</em>-intermediate by the amino group and subsequent aromatization <em>via</em> [1,2]-alkyl shift. Several of the synthesized quinolino[4,3,2-<em>kl</em>]acridines showed high antibacterial activity against <em>S. epidermidis</em> ATCC 29887 and <em>M. smegmatis</em> mc<sup>2</sup> 155.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155904"},"PeriodicalIF":1.5,"publicationDate":"2025-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145681801","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":"2025-11-17","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}
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":"2025-11-16","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 : 2025-11-15DOI: 10.1016/j.tetlet.2025.155895
Peng Xu , Xu-Long Qin
Organic electrochemistry has attracted increasing attention as a novel strategy to replace traditional chemical oxidants and reductants in organic synthesis, thereby avoiding employing stoichiometric amounts of toxic reagents. In particular, electrochemical transition metal-catalyzed CH functionalization assisted by bidentate directing groups provides an efficient and straightforward approach for transforming abundant organic molecules into various functional groups. This review summarizes recent advances in electrochemical, transition-metal-catalyzed CH functionalization mediated by bidentate directing groups, focusing on CX (X = C, N, O) bond formation.
{"title":"Recent advances in electrochemical earth-abundant metal catalysis for CX (X = C, N, O) bond formation via bidentate directing groups","authors":"Peng Xu , Xu-Long Qin","doi":"10.1016/j.tetlet.2025.155895","DOIUrl":"10.1016/j.tetlet.2025.155895","url":null,"abstract":"<div><div>Organic electrochemistry has attracted increasing attention as a novel strategy to replace traditional chemical oxidants and reductants in organic synthesis, thereby avoiding employing stoichiometric amounts of toxic reagents. In particular, electrochemical transition metal-catalyzed C<img>H functionalization assisted by bidentate directing groups provides an efficient and straightforward approach for transforming abundant organic molecules into various functional groups. This review summarizes recent advances in electrochemical, transition-metal-catalyzed C<img>H functionalization mediated by bidentate directing groups, focusing on C<img>X (X = C, N, O) bond formation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155895"},"PeriodicalIF":1.5,"publicationDate":"2025-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576487","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":"2025-11-14","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 : 2025-11-14DOI: 10.1016/j.tetlet.2025.155900
Qing Wei , Ping Ying , Yunpeng Sun , Mengmeng Yu , Letian Cui , Xiaoli Sun , Qiang Zheng , Lingyi Kong , Jun Luo
Mufolinoids W and X (1 and 2), two new trinortriterpenoids, along with their biosynthetic precursor triterpenoids (3 and 4), were isolated and identified from the medicinal plant Munronia unifoliolata Oliv.—a species used in Traditional Chinese Medicine for treating rheumatic arthritis pain and traumatic injuries. Their structures were identified by high-resolution mass spectrometry (HR-MS), one-dimensional/two-dimensional nuclear magnetic resonance (1D/2D NMR), and experimental and calculated electronic circular dichroism (ECD) methods. Structurally, 1 and 2 were the second example of 3/4-seco trinortriterpenoids from the plant kingdom. Biologically, the inhibitory effects of 1 and 2 on nitric oxide (NO) production and their multidrug resistance reversal activity were evaluated and screened.
{"title":"Two new trinortriterpenoids from Munronia unifoliolata","authors":"Qing Wei , Ping Ying , Yunpeng Sun , Mengmeng Yu , Letian Cui , Xiaoli Sun , Qiang Zheng , Lingyi Kong , Jun Luo","doi":"10.1016/j.tetlet.2025.155900","DOIUrl":"10.1016/j.tetlet.2025.155900","url":null,"abstract":"<div><div>Mufolinoids W and X (<strong>1</strong> and <strong>2</strong>), two new trinortriterpenoids, along with their biosynthetic precursor triterpenoids (<strong>3</strong> and <strong>4</strong>), were isolated and identified from the medicinal plant <em>Munronia unifoliolata</em> Oliv.—a species used in Traditional Chinese Medicine for treating rheumatic arthritis pain and traumatic injuries. Their structures were identified by high-resolution mass spectrometry (HR-MS), one-dimensional/two-dimensional nuclear magnetic resonance (1D/2D NMR), and experimental and calculated electronic circular dichroism (ECD) methods. Structurally, <strong>1</strong> and <strong>2</strong> were the second example of 3/4-seco trinortriterpenoids from the plant kingdom. Biologically, the inhibitory effects of <strong>1</strong> and <strong>2</strong> on nitric oxide (NO) production and their multidrug resistance reversal activity were evaluated and screened.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155900"},"PeriodicalIF":1.5,"publicationDate":"2025-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576585","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 : 2025-11-13DOI: 10.1016/j.tetlet.2025.155898
Peng Xu , Yu-Xing Chen , Xuan Ni , Xu-Long Qin
P-Stereogenic phosphorus compounds are important chiral ligands and highly efficient small molecule organocatalysts. In this study, we report Pd(II)-catalyzed enantioselective C(sp2)−H arylation of phosphinamide using directing group with diaryliodonium triflates. The reaction employs an inexpensive commercially available L-Phe-OH derivative as the chiral ligand. Through desymmetrization, this method was verified to afford the desired products in moderate yield with good enantioselectivity, demonstrating broad substrate scope and improved functional group tolerance.
p -立体源性磷化合物是重要的手性配体和高效的小分子有机催化剂。在这项研究中，我们报道了Pd（II）催化的磷酰胺的对映选择性C(sp2)−H基化与三氟酸二芳基碘酮。该反应采用一种廉价的市售l -苯基- oh衍生物作为手性配体。通过反对称，验证了该方法能以中等产率、良好的对映体选择性、较宽的底物范围和较好的官能团耐受性得到所需的产物。
{"title":"Pd(II)-catalyzed enantioselective C(sp2)–H ortho arylation toward the synthesis of P-stereogenic phosphinamides","authors":"Peng Xu , Yu-Xing Chen , Xuan Ni , Xu-Long Qin","doi":"10.1016/j.tetlet.2025.155898","DOIUrl":"10.1016/j.tetlet.2025.155898","url":null,"abstract":"<div><div><em>P</em>-Stereogenic phosphorus compounds are important chiral ligands and highly efficient small molecule organocatalysts. In this study, we report Pd(II)-catalyzed enantioselective C(sp<sup>2</sup>)−H arylation of phosphinamide using directing group with diaryliodonium triflates. The reaction employs an inexpensive commercially available <em>L</em>-Phe-OH derivative as the chiral ligand. Through desymmetrization, this method was verified to afford the desired products in moderate yield with good enantioselectivity, demonstrating broad substrate scope and improved functional group tolerance.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155898"},"PeriodicalIF":1.5,"publicationDate":"2025-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576486","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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