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Microwave-assisted synthesis of pyrrolidinyl-spirooxindoles via tandem 1,3-dipolar cycloaddition and oxidative dehydrogenation 通过串联 1,3-二极环加成和氧化脱氢微波辅助合成吡咯烷基螺氧吲哚
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-14 DOI: 10.1016/j.tet.2024.134379
Hong-bo Tan , Yu-heng Xiang , Jing-wen Huang , Si-ying Ren , Chang-qiu Lin , Zhi-gang Xu , Dian-yong Tang , Zhong-zhu Chen
{"title":"Microwave-assisted synthesis of pyrrolidinyl-spirooxindoles via tandem 1,3-dipolar cycloaddition and oxidative dehydrogenation","authors":"Hong-bo Tan ,&nbsp;Yu-heng Xiang ,&nbsp;Jing-wen Huang ,&nbsp;Si-ying Ren ,&nbsp;Chang-qiu Lin ,&nbsp;Zhi-gang Xu ,&nbsp;Dian-yong Tang ,&nbsp;Zhong-zhu Chen","doi":"10.1016/j.tet.2024.134379","DOIUrl":"10.1016/j.tet.2024.134379","url":null,"abstract":"<div><div>An oxidant-free, microwave-promoted tandem 1,3-dipolar cycloaddition and dehydrogenation oxidation is achieved under environmentally friendly conditions, delivering novel fused pyrrolidinyl-spirooxindoles in good to excellent yields. This work provides powerful means to expand the structural diversity of pyrrolidinyl-spirooxindole as a promising scaffold for novel drug discovery.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134379"},"PeriodicalIF":2.1,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes 用于苯并[b]氮杂卓和 1，3-共轭二烯歧化合成的催化剂控制型可切换形式逆-布赫纳反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-13 DOI: 10.1016/j.tet.2024.134378
Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie
{"title":"Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes","authors":"Zhaoxue Wang ,&nbsp;Menghui Guo ,&nbsp;Ping Wu ,&nbsp;Rui Yan ,&nbsp;Guili Zhao ,&nbsp;Ming Liu ,&nbsp;Yilei Xiao ,&nbsp;Lingang Wu ,&nbsp;Lei Xie","doi":"10.1016/j.tet.2024.134378","DOIUrl":"10.1016/j.tet.2024.134378","url":null,"abstract":"<div><div>Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with <em>N</em>-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[<em>b</em>]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134378"},"PeriodicalIF":2.1,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657309","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Anticancer activity of the synthetic kusunokinin analogues on human cancer cell lines 人工合成的 Kusunokinin 类似物对人类癌细胞株的抗癌活性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-13 DOI: 10.1016/j.tet.2024.134362
Patpanat Sermmai , Kornthip Tangthana-umrung , Anawat Tailangka , Thidarath Rattanaburee , Chompunud Chompunud Na Ayudhya , Kulvadee Dolsophon , Varomyalin Tipmanee , Potchanapond Graidist , Tienthong Thongpanchang
{"title":"Anticancer activity of the synthetic kusunokinin analogues on human cancer cell lines","authors":"Patpanat Sermmai ,&nbsp;Kornthip Tangthana-umrung ,&nbsp;Anawat Tailangka ,&nbsp;Thidarath Rattanaburee ,&nbsp;Chompunud Chompunud Na Ayudhya ,&nbsp;Kulvadee Dolsophon ,&nbsp;Varomyalin Tipmanee ,&nbsp;Potchanapond Graidist ,&nbsp;Tienthong Thongpanchang","doi":"10.1016/j.tet.2024.134362","DOIUrl":"10.1016/j.tet.2024.134362","url":null,"abstract":"<div><div>The series of racemic kusunokinin derivatives were synthesized and their cytotoxic activities and cell viability on cancer cells including breast cancer (MCF-7, MDA-MB468), colon cancer (HT-29), cholangiocarcinoma (KKU-M213) and ovarian cancer (A2780) cells were investigated. The results showed that compounds <strong>6aa</strong>, <strong>6da</strong>, and <strong>6de</strong> exhibited growth inhibition against breast cancer (MDA-MB468), cholangiocarcinoma (KKU-M213), colon cancer (HT-29), and ovarian cancer (A2780) cells with IC50 values (<em>μ</em>M) 13.77 ± 0.38, 7.94 ± 0.45, and 4.22 ± 0.13 (MDA-MB468); 4.21 ± 0.21, 0.97 ± 0.03, and 0.09 ± 0.02 (KKU-M213); 22.66 ± 0.23, and 15.62 ± 0.06 (HT-29); 13.11 ± 0.37, 11.51 ± 0.43, and 1.87 ± 0.01 (A2780); respectively. Interestingly, a positive control, doxorubicin, showed less cytotoxicity than <strong>6da</strong> and <strong>6de</strong> on cholangiocarcinoma KKU-M213 and ovarian cancer A2780 cells. Moreover, these three synthetic compounds also exhibited less toxicity than doxorubicin on the normal cells, MMNK-1, Vero and L-929. The binding possibility towards CSF1R, <strong>6de</strong> (−11.59 kcal/mol) and <em>trans</em>-(−)-kusunokinin (−11.75 kcal/mol) were similar in both docking energies and docking poses. <strong>6de</strong> interacted with Trp550 <em>via</em> π-π stacking in the similar manner with <em>trans</em>-(−)-kusunokinin and <em>trans</em>-(+)-kusunokinin.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"170 ","pages":"Article 134362"},"PeriodicalIF":2.1,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142719772","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 orthoformate-bridged bis-diazeniumdiolates: Enhanced nitric oxide loading and released NO under physiological conditions 一种原甲酸酯桥接的双偶氮二元醇：生理条件下增强的一氧化氮负荷和释放的一氧化氮
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-10 DOI: 10.1016/j.tet.2024.134367
En Chen , Qi Zhu , Luyi Zhan , Jun Chen , Huajing Lv , Wenteng Chen , Yongping Yu
{"title":"An orthoformate-bridged bis-diazeniumdiolates: Enhanced nitric oxide loading and released NO under physiological conditions","authors":"En Chen ,&nbsp;Qi Zhu ,&nbsp;Luyi Zhan ,&nbsp;Jun Chen ,&nbsp;Huajing Lv ,&nbsp;Wenteng Chen ,&nbsp;Yongping Yu","doi":"10.1016/j.tet.2024.134367","DOIUrl":"10.1016/j.tet.2024.134367","url":null,"abstract":"<div><div>Diazeniumdiolates are highly valued as NO donors in biomedical applications because of their exceptional NO-loading efficiency. Typically, the NO-releasing properties of these compounds can be tailored by incorporating various substitutes at the O<sup>2</sup>-position of <em>N</em>-diazeniumdiolates. In this study, we report a novel class of bis-diazeniumdiolates, which are covalently linked through an orthoformate-bridge between two diazeniumdiolate groups. Under physiological conditions (pH = 7.4, 37 <sup>°</sup>C), these orthoformate-bridged bis-diazeniumdiolates were found to release four equivalents of NO. The half-lives of NO release varied between 1.3 and 17.9 min. Furthermore, these bis-diazeniumdiolates exhibited superior bactericidal activity against <em>Escherichia coli</em> (MIC = 1–8 mM, MBC = 8–32 mM) and <em>Staphylococcus aureus</em> (MIC = 2–8 mM, MBC = 16–32 mM) compared to the commercial 2-(<em>N, N</em>-diethylamino)-diazenolate-2-oxide, which only releases two equivalents of NO per molecular (MIC <sub>(<em>E. coli</em>)</sub> = 32 mM, MIC <sub>(<em>S.aureus</em>)</sub> = 64 mM, MBC = 128 mM). These bis-diazeniumdiolates enhance NO loading and release NO independently of enzymes or chemical additives, indicating their potential benefits for further biomedical applications.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134367"},"PeriodicalIF":2.1,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657410","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Bio-synthesized Fe(0)/Fe2O3 composite nanoparticles as a catalyst towards the preparation of dihydropyridine derivatives under solvent-free condition at room temperature 以生物合成的 Fe(0)/Fe2O3 复合纳米粒子为催化剂，在室温无溶剂条件下制备二氢吡啶衍生物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-10 DOI: 10.1016/j.tet.2024.134365
Partha Sarathi Bera, Jharna Mahato, Tanmoy Kumar Saha
{"title":"Bio-synthesized Fe(0)/Fe2O3 composite nanoparticles as a catalyst towards the preparation of dihydropyridine derivatives under solvent-free condition at room temperature","authors":"Partha Sarathi Bera,&nbsp;Jharna Mahato,&nbsp;Tanmoy Kumar Saha","doi":"10.1016/j.tet.2024.134365","DOIUrl":"10.1016/j.tet.2024.134365","url":null,"abstract":"<div><div>A sustainable and innovative approach has been developed for synthesizing of Fe(0)/Fe<sub>2</sub>O<sub>3</sub> composite nanoparticles (Fe(0)/Fe<sub>2</sub>O<sub>3</sub>NPs), utilizing the bark extract of the arjun tree (<em>Terminalia arjuna</em>) as a reducing and capping agent. This environmentally friendly Fe(0)/Fe<sub>2</sub>O<sub>3</sub>NPs was thoroughly characterized using various analytical techniques, including UV–Visible spectroscopy, FT-IR, PXRD, HR-TEM, SEM, and XPS. The nanoparticles were then evaluated as catalysts for facilitating the three-component Hantzsch reaction with acetylacetone, ammonium acetate, and substituted aldehydes, producing bioactive dihydropyridine derivatives. The catalyst exhibited high performance over approximately five cycles, with negligible loss in yield and catalytic efficiency. Additionally, a mechanistic pathway was proposed and elucidated through intermediate mass analysis, supported by Density Functional Theory (DFT) calculations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134365"},"PeriodicalIF":2.1,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657405","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 the indole alkaloid isolated from the marine sponge Halichondria melanodocia 从海洋海绵 Halichondria melanodocia 中分离出的吲哚生物碱的合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-10 DOI: 10.1016/j.tet.2024.134368
Gordon W. Gribble, Stephen W. Wright
{"title":"Synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia","authors":"Gordon W. Gribble,&nbsp;Stephen W. Wright","doi":"10.1016/j.tet.2024.134368","DOIUrl":"10.1016/j.tet.2024.134368","url":null,"abstract":"<div><div>We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge <em>Halichondria melanodocia</em>, using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a <em>sp</em><sup><em>2</em></sup> iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134368"},"PeriodicalIF":2.1,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657307","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Anthelmintic activity of selected neolignans and semisynthetic derivatives from Styrax suberifolius 从鼠李属植物中提取的部分新木质素及其半合成衍生物的驱虫活性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-09 DOI: 10.1016/j.tet.2024.134366
Kanchana Wijesekera , Aya C. Taki , Joseph J. Byrne , Jonathan M. White , Anthony R. Carroll , Robin B. Gasser , Rohan A. Davis
{"title":"Anthelmintic activity of selected neolignans and semisynthetic derivatives from Styrax suberifolius","authors":"Kanchana Wijesekera ,&nbsp;Aya C. Taki ,&nbsp;Joseph J. Byrne ,&nbsp;Jonathan M. White ,&nbsp;Anthony R. Carroll ,&nbsp;Robin B. Gasser ,&nbsp;Rohan A. Davis","doi":"10.1016/j.tet.2024.134366","DOIUrl":"10.1016/j.tet.2024.134366","url":null,"abstract":"<div><div>The plant metabolite, equiselignan B (<strong>2</strong>), isolated from the fruits of <em>Styrax suberifolius</em> was used to generate a semisynthetic library. Extraction and purification studies yielded large quantities (∼70 mg) of <strong>2</strong>, a new glycoside, suberifolioside A (<strong>1</strong>), and the previously described neolignan egonol (<strong>3</strong>). The planer structure of <strong>1</strong> was established following 1D/2D NMR and MS analyses, and its absolute configuration was determined by X-ray diffraction studies. Acid hydrolysis of <strong>1</strong> yielded an additional amount of scaffold <strong>2</strong> (436 mg) that was subsequently converted into seven new ether derivatives (<strong>4</strong>–<strong>10</strong>) and two new ester derivatives (<strong>11</strong>–<strong>12</strong>) using commercially available alkyl halides and acyl chlorides, respectively. The chemical structures of the new semisynthetic ether and ester derivatives were assigned by spectroscopic and spectrometric analyses. Subsequently, compounds <strong>1</strong>–<strong>12</strong> were evaluated for their anthelmintic activity on exsheathed third-stage larvae (xL3s) and fourth-stage larvae (L4s) of <em>Haemonchus contortus</em> (barber's pole worm) – a highly pathogenic parasitic roundworm of ruminant livestock. Ether derivative <strong>5</strong> displayed significant anthelmintic activity against both xL3s and L4s, resulting in a 66–73 % reduction in motility at 50 μM after 168 h (xL3s) or 90 h (L4s) of exposure and IC<sub>50</sub> values of 24–30 μM. This derivative also induced curved (<em>Cur</em>), evisceration (<em>Evi</em>) and skinny (<em>Ski</em>) phenotypes in affected larvae. Compounds <strong>1</strong>, <strong>9</strong> and <strong>12</strong> also had marked activity against L4s, which indicate that the neolignan structure class warrants further investigation for anthelmintic activity.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134366"},"PeriodicalIF":2.1,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657406","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Recent developments in the metal-free synthesis of oxazoles 草唑无金属合成的最新进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-09 DOI: 10.1016/j.tet.2024.134363
Pravin J. Wanjari , Kriti Mehta , Marudhvathi Kudumula , Rohit Sharma , Prasad V. Bharatam
{"title":"Recent developments in the metal-free synthesis of oxazoles","authors":"Pravin J. Wanjari ,&nbsp;Kriti Mehta ,&nbsp;Marudhvathi Kudumula ,&nbsp;Rohit Sharma ,&nbsp;Prasad V. Bharatam","doi":"10.1016/j.tet.2024.134363","DOIUrl":"10.1016/j.tet.2024.134363","url":null,"abstract":"<div><div>Oxazoles found a very prominent position in heterocyclic and medicinal chemistry. Several methods of synthesizing these species were introduced, and recent efforts have been made to generate these species using metal-free methods in a highly efficient manner. In the past decade, many novel metal-free methods of synthesizing oxazoles have been emerged. A cursory glance at these methods indicated that it is possible to classify the reported methods on the basis of the proposed mechanisms. This review provides an overview of all these methods along with mechanistic details and tries to find some commonalities among these.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134363"},"PeriodicalIF":2.1,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657408","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides 可回收 Ag/GO-NH2 与胺和 H-膦氧化物催化苄醇的多组分氨基膦酰化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134359
Qiang Huang , Lei Zhu , Zhonghua Shi , Xin Jin , Wenwu Zhong
{"title":"Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides","authors":"Qiang Huang ,&nbsp;Lei Zhu ,&nbsp;Zhonghua Shi ,&nbsp;Xin Jin ,&nbsp;Wenwu Zhong","doi":"10.1016/j.tet.2024.134359","DOIUrl":"10.1016/j.tet.2024.134359","url":null,"abstract":"<div><div>An Ag nanoparticles immobilized heterogeneous composite (Ag/GO-NH<sub>2</sub>) was synthesized by anchoring nitrogen-containing small molecule onto graphene. The prepared Ag/GO-NH<sub>2</sub> was characterized by FT-IR, XRD, SEM and TEM, identifying its structure and composition. Remarkably, the Ag/GO-NH<sub>2</sub> composite emerged as a heterogeneous catalyst, they can promote the multi-component aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides. This heterogeneous catalytic system demonstrated good functional group tolerance and broad substrate scope, affording various α-aminophosphine oxides in good yields. Additionally, the nanocatalyst can be recovered and reused without significant decrease performance of the reaction. It offers an alternative and promising strategy for the heterogeneous synthesis of α-aminophosphine oxides.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134359"},"PeriodicalIF":2.1,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Electrochemical-promoted Mannich-type three-component reaction of benzo-fused cyclic amides using methanol as C1 source instead of formaldehyde 用甲醇代替甲醛作为 C1 源，电化学促进苯并融合环酰胺的曼尼希式三组分反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134357
Yahui Sang , Jinjin Zhang , Mengjia Zhao , Haijuan Qin , Chao Chen , Wei Liu
{"title":"Electrochemical-promoted Mannich-type three-component reaction of benzo-fused cyclic amides using methanol as C1 source instead of formaldehyde","authors":"Yahui Sang ,&nbsp;Jinjin Zhang ,&nbsp;Mengjia Zhao ,&nbsp;Haijuan Qin ,&nbsp;Chao Chen ,&nbsp;Wei Liu","doi":"10.1016/j.tet.2024.134357","DOIUrl":"10.1016/j.tet.2024.134357","url":null,"abstract":"<div><div>The three-component <em>N</em>-Mannich reaction is provided in an electrochemical variant. The corresponding <em>N</em>-Mannich base products were obtained by the one-pot method of benzo-fused cyclic amides with secondary amines under a small current of 3 mA using methanol as the carbon source. The reaction is simple to carry out (room temperature and air environment) and requires no supporting electrolytes, using TEMPO as the oxidizing agent. The substrate scope is wide, and the yield is good (39 cases, up to 99 %). CV experiments show that secondary amines are oxidized first at the anode. Moreover, this reaction can be scaled up to the grams.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134357"},"PeriodicalIF":2.1,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657402","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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