首页 > 最新文献

Synlett最新文献

英文 中文
Deucravacitinib Induces Proteasomal Degradation of YAP1 in Human Glioblastoma Cells 去氯伐替尼诱导人胶质母细胞瘤细胞中 YAP1 的蛋白酶体降解
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-22 DOI: 10.1055/a-2331-6463
Shaonan Wang, Min Sun, Yajuan Su, Zhou Xu, Ang Li, Weiwei He
Deucravacitinib is a selective allosteric inhibitor of tyrosine kinase 2 (TYK2) recently approved by the FDA for the treatment of plaque psoriasis. We discovered that this compound induces proteasomal degradation of YAP1, the downstream effector of the Hippo signaling pathway, in human glioblastoma (GBM) cells (U-87 MG). This degradation is independent of the canonical Hippo pathway, which offers clues to alternative mechanisms for YAP1 regulation.
Deucravacitinib 是酪氨酸激酶 2 (TYK2) 的一种选择性异位抑制剂,最近被美国食品及药物管理局批准用于治疗斑块型银屑病。我们发现,这种化合物能诱导人胶质母细胞瘤(GBM)细胞(U-87 MG)中希波信号通路下游效应因子 YAP1 蛋白质体降解。这种降解独立于典型的 Hippo 通路,为 YAP1 的替代调控机制提供了线索。
{"title":"Deucravacitinib Induces Proteasomal Degradation of YAP1 in Human Glioblastoma Cells","authors":"Shaonan Wang, Min Sun, Yajuan Su, Zhou Xu, Ang Li, Weiwei He","doi":"10.1055/a-2331-6463","DOIUrl":"https://doi.org/10.1055/a-2331-6463","url":null,"abstract":"Deucravacitinib is a selective allosteric inhibitor of tyrosine kinase 2 (TYK2) recently approved by the FDA for the treatment of plaque psoriasis. We discovered that this compound induces proteasomal degradation of YAP1, the downstream effector of the Hippo signaling pathway, in human glioblastoma (GBM) cells (U-87 MG). This degradation is independent of the canonical Hippo pathway, which offers clues to alternative mechanisms for YAP1 regulation.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141112368","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
Copper−Promoted Dimerization of Benzyl Thiocyanates to Access Functionalized Bibenzyls 铜促进硫氰酸苄酯二聚化以获得官能化的比本苄
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-21 DOI: 10.1055/a-2330-9955
Sandeep Singh, S. R. De
The synthesis of bibenzyl derivatives holds significance in organic chemistry due to their diverse pharmacological and synthetic applications. Herein, we report a novel copper–promoted dimerization reaction for the efficient synthesis of functionalized bibenzyls from benzyl thiocyanates. The coupling reaction proceeds under aerobic and mild conditions via cascade C–S bond cleavage in one pot. Diverse substituents including electron–withdrawing groups on the aryl ring are well–tolerated to afford the desired products in moderate to good yields. The developed protocol could be utilized to obtain the cross coupling product from two different electron–deficient benzyl thiocyanates.
由于联苄衍生物具有多种药理和合成应用,因此其合成在有机化学中具有重要意义。在此,我们报告了一种新型的铜促进二聚反应,用于从硫氰酸苄酯高效合成功能化的联苄。该偶联反应在有氧和温和的条件下通过级联 C-S 键裂解在一锅中进行。芳基环上的各种取代基(包括抽电子基团)都能很好地耐受,从而以中等至较高的产率得到所需的产物。所开发的方案可用于从两种不同的缺电子硫氰酸苄酯中获得交叉偶联产物。
{"title":"Copper−Promoted Dimerization of Benzyl Thiocyanates to Access Functionalized Bibenzyls","authors":"Sandeep Singh, S. R. De","doi":"10.1055/a-2330-9955","DOIUrl":"https://doi.org/10.1055/a-2330-9955","url":null,"abstract":"The synthesis of bibenzyl derivatives holds significance in organic chemistry due to their diverse pharmacological and synthetic applications. Herein, we report a novel copper–promoted dimerization reaction for the efficient synthesis of functionalized bibenzyls from benzyl thiocyanates. The coupling reaction proceeds under aerobic and mild conditions via cascade C–S bond cleavage in one pot. Diverse substituents including electron–withdrawing groups on the aryl ring are well–tolerated to afford the desired products in moderate to good yields. The developed protocol could be utilized to obtain the cross coupling product from two different electron–deficient benzyl thiocyanates.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141116655","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 Substituted Cyclooctenes through Cross-Coupling Reactions 通过交叉偶联反应合成取代的环辛烯
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-18 DOI: 10.1055/a-2330-0819
Ryuichi Murata, Rakuto Yoshida, Daisuke Uraguchi, Keisuke Asano
Cross-coupling methods for the introduction of various substituents into the olefin moiety of cyclooctenes were developed. A range of 1-substituted cis-cyclooctenes were synthesized. These protocols unlocked routes to previously inaccessible derivatives, allowing for the syntheses of cis-cyclooctenes bearing various functional groups. Moreover, the method was applied to the synthesis of a 1,2-disubstituted trans-cyclooctene for the first time, which proved to be a significantly active organocatalyst in relation to the previously developed monosubstituted trans-cyclooctene.
开发了在环辛烯的烯烃分子中引入各种取代基的交叉偶联方法。合成了一系列 1-取代的顺式环辛烯。这些方法开辟了以前无法获得的衍生物的途径,从而可以合成带有各种官能团的顺式环辛烯。此外,该方法还首次应用于合成 1,2-二取代的反式环辛烯,与之前开发的单取代反式环辛烯相比,它被证明是一种活性显著的有机催化剂。
{"title":"Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions","authors":"Ryuichi Murata, Rakuto Yoshida, Daisuke Uraguchi, Keisuke Asano","doi":"10.1055/a-2330-0819","DOIUrl":"https://doi.org/10.1055/a-2330-0819","url":null,"abstract":"Cross-coupling methods for the introduction of various substituents into the olefin moiety of cyclooctenes were developed. A range of 1-substituted cis-cyclooctenes were synthesized. These protocols unlocked routes to previously inaccessible derivatives, allowing for the syntheses of cis-cyclooctenes bearing various functional groups. Moreover, the method was applied to the synthesis of a 1,2-disubstituted trans-cyclooctene for the first time, which proved to be a significantly active organocatalyst in relation to the previously developed monosubstituted trans-cyclooctene.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141124948","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 Dihydrobenzosiloles and Silacyclopentane via Double Hydroalumination of Terminal Alkynes 通过末端炔烃的双氢化氨合成二氢苯甲硅烷和硅杂环戊烷
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-18 DOI: 10.1055/a-2330-0874
Ryusei Osawa, Kotaro Ogihara, Fumine Hamasaki, H. Kinoshita, Katsukiyo Miura
We developed an efficient method for the synthesis of dihydrobenzosiloles in 19% to 90% isolated yields from 1-hydrosilyl-2-ethynylbenzenes using two equivalents of diisobutylaluminum hydride. The reaction mechanism involves regioselective double hydroalumination of the alkyne moiety followed by cyclization to 2-alanyldihydrobenzosilole. A silacyclopentane was also synthesized in 97% isolated yield from the corresponding 4-silylbut-1-yne under the same reaction conditions. Although the substrate scope was conducted on a 0.5 mmol scale, a gram-scale reaction of 1-diphenylsilyl-2-ethynylbenzene under the optimized reaction conditions successfully afforded the desired product in 94% isolated yield without loss of reactivity.
我们开发了一种高效的方法,利用两个当量的二异丁基氢化铝,从 1- 氢硅烷基-2-乙炔基苯合成二氢苯甲硅烷基,分离产率为 19% 至 90%。反应机理包括炔基的区域选择性双氢化,然后环化成 2-丙烯基二氢苯甲硅醚。在相同的反应条件下,还从相应的 4-硅基丁基-1-炔合成出了一种硅基环戊烷,分离收率为 97%。虽然底物范围是在 0.5 毫摩尔的规模下进行的,但在优化的反应条件下,1-二苯基硅基-2-乙炔基苯的克级反应成功地得到了所需的产物,分离收率为 94%,且没有失去反应活性。
{"title":"Synthesis of Dihydrobenzosiloles and Silacyclopentane via Double Hydroalumination of Terminal Alkynes","authors":"Ryusei Osawa, Kotaro Ogihara, Fumine Hamasaki, H. Kinoshita, Katsukiyo Miura","doi":"10.1055/a-2330-0874","DOIUrl":"https://doi.org/10.1055/a-2330-0874","url":null,"abstract":"We developed an efficient method for the synthesis of dihydrobenzosiloles in 19% to 90% isolated yields from 1-hydrosilyl-2-ethynylbenzenes using two equivalents of diisobutylaluminum hydride. The reaction mechanism involves regioselective double hydroalumination of the alkyne moiety followed by cyclization to 2-alanyldihydrobenzosilole. A silacyclopentane was also synthesized in 97% isolated yield from the corresponding 4-silylbut-1-yne under the same reaction conditions. Although the substrate scope was conducted on a 0.5 mmol scale, a gram-scale reaction of 1-diphenylsilyl-2-ethynylbenzene under the optimized reaction conditions successfully afforded the desired product in 94% isolated yield without loss of reactivity.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141125001","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
Organocatalytic Fischer Indolization Using the 2,2′-Biphenol/ B(OH)3 System 使用 2,2′-联苯酚/B(OH)3 系统的有机催化费舍尔吲哚化反应
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-17 DOI: 10.1055/s-0043-1775363
Kenji Sugimoto, Yuji Matsuya, Yusei Wada, Fumino Kitamura
An organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)3 (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO4, which efficiently scavenges NH3 (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.y
通过将 2,2′-联苯酚 (10 mol%) 和 B(OH)3 (30 mol%) 作为弱酸、易得酸和易于处理的酸结合在一起,建立了一种有机催化的费歇尔吲哚化反应。MgSO4 能有效清除 NH3(一种可能的酸催化剂毒物),加入 MgSO4 似乎是这一工艺成功的关键。使用这种方法可以获得相应的吲哚,产率高达 91%。
{"title":"Organocatalytic Fischer Indolization Using the 2,2′-Biphenol/ B(OH)3 System","authors":"Kenji Sugimoto, Yuji Matsuya, Yusei Wada, Fumino Kitamura","doi":"10.1055/s-0043-1775363","DOIUrl":"https://doi.org/10.1055/s-0043-1775363","url":null,"abstract":"An organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)3 (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO4, which efficiently scavenges NH3 (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.y","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140963108","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
Generation of Carbamoyl Radicals and 3,4-Dihydroquinolin-2(1H)-ones Enabled by Iron Photoredox Catalysis 通过铁光氧化催化生成氨基甲酰基自由基和 3,4-二氢喹啉-2(1H)-酮
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-16 DOI: 10.1055/s-0043-1763753
Tao Cai, Gaofeng Feng, Yanhua Fu, Chao Zhang
A new protocol for accessing 3,4-dihydroquinolin-2(1H)-ones was established through a sequence of iron-catalyzed photoredox generation of carbamoyl radicals from oxamic acids, addition of the carbamoyl radicals to electron-deficient alkenes, intramolecular cyclization, and aromatization. The process is compatible with a variety of N-phenyloxamic acids and monosubstituted, 1,1-disubstituted, and trisubstituted electron-deficient alkenes. Employing cheap, readily available, and environmentally benign iron as the catalyst, the protocol provides an excellent alternative for synthesis of 3,4-dihydroquinolin-2(1H)-ones.
通过铁催化氧肟酸产生氨基甲酰基、氨基甲酰基加入缺电子烯、分子内环化和芳香化的一系列过程,建立了一种获得 3,4-二氢喹啉-2(1H)-酮的新方法。该工艺适用于各种 N-苯基氧肟酸和单取代、1,1-二取代和三取代缺电子烯。该方法采用廉价、易得、对环境无害的铁作为催化剂,为合成 3,4-二氢喹啉-2(1H)-酮提供了一个极佳的替代方案。
{"title":"Generation of Carbamoyl Radicals and 3,4-Dihydroquinolin-2(1H)-ones Enabled by Iron Photoredox Catalysis","authors":"Tao Cai, Gaofeng Feng, Yanhua Fu, Chao Zhang","doi":"10.1055/s-0043-1763753","DOIUrl":"https://doi.org/10.1055/s-0043-1763753","url":null,"abstract":"A new protocol for accessing 3,4-dihydroquinolin-2(1H)-ones was established through a sequence of iron-catalyzed photoredox generation of carbamoyl radicals from oxamic acids, addition of the carbamoyl radicals to electron-deficient alkenes, intramolecular cyclization, and aromatization. The process is compatible with a variety of N-phenyloxamic acids and monosubstituted, 1,1-disubstituted, and trisubstituted electron-deficient alkenes. Employing cheap, readily available, and environmentally benign iron as the catalyst, the protocol provides an excellent alternative for synthesis of 3,4-dihydroquinolin-2(1H)-ones.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140970643","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
Metal-Free Synthesis of C-3-Alkoxycarbonylated 2H-Indazoles Using Alkyl Carbazates 使用烷基咔嗪酸盐无金属合成 C-3-烷氧基羰基 2H-Indazoles
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-16 DOI: 10.1055/a-2316-5066
Dipti Lai, Suvam Bhattacharjee, Sumit Ghosh, Subrata Sinha, Alakananda Hajra

A simple, efficient, and environmentally benign method for the direct C-3-alkoxycarbonylation of 2H-indazoles using alkyl carbazates has been developed under metal-free conditions at room temperature. This current protocol represents a facile access to C-3-carboxylic ester derived 2H-indazoles with wide functional group tolerance in good to excellent yields. The mechanistic studies suggest that the reaction proceeds through a radical pathway.

在室温无金属条件下,利用烷基咔嗪酸盐直接对 2H-indazoles 进行 C-3-alkoxycarbonylation 的简单、高效和环保方法已经开发出来。目前的这一方法可以方便地获得 C-3-羧酸酯衍生的 2H-吲唑,且具有广泛的官能团耐受性,收率良好甚至极佳。机理研究表明,反应是通过自由基途径进行的。
{"title":"Metal-Free Synthesis of C-3-Alkoxycarbonylated 2H-Indazoles Using Alkyl Carbazates","authors":"Dipti Lai, Suvam Bhattacharjee, Sumit Ghosh, Subrata Sinha, Alakananda Hajra","doi":"10.1055/a-2316-5066","DOIUrl":"https://doi.org/10.1055/a-2316-5066","url":null,"abstract":"<p>A simple, efficient, and environmentally benign method for the direct C-3-alkoxycarbonylation of 2<i>H</i>-indazoles using alkyl carbazates has been developed under metal-free conditions at room temperature. This current protocol represents a facile access to C-3-carboxylic ester derived 2<i>H</i>-indazoles with wide functional group tolerance in good to excellent yields. The mechanistic studies suggest that the reaction proceeds through a radical pathway.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141062053","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
Ultrasound-Assisted, BF3·OEt2-Promoted, Multicomponent Synthesis of Chromene-Based Podophyllotoxin Analogues 超声波辅助、BF3-OEt2 促进、多组分合成基于色烯的鬼臼毒素类似物
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-16 DOI: 10.1055/s-0043-1774865
RS Laurentiz, Fernanda A. Santos
A novel method was developed to synthesise chromene-lactone analogues of podophyllotoxin using an ultrasound-assisted multicomponent reaction (MCR). The MCR involved tetronic acid, phenols, and aromatic aldehydes and was promoted by BF3·OEt2, resulting in the production of ten derivatives with different substituents on the aromatic rings in yields ranging from 32% to 93%. These compounds are of interest due to their reported activity against tumour cells. Their ease of synthesis through the MCR may allow for more in-depth studies on anticancer activity, as well as investigations of other biological targets. The synthesised derivatives contain important pharmacophoric groups for potential applications in medicinal chemistry.
本研究采用超声辅助多组分反应(MCR)开发了一种合成荚叶内酯类似物的新方法。在 BF3-OEt2 的促进下,该多组分反应涉及四酸、酚和芳香醛,生成了 10 种芳香环上具有不同取代基的衍生物,产率在 32% 至 93% 之间。据报道,这些化合物具有抗肿瘤细胞的活性,因此备受关注。通过 MCR 方法轻松合成这些化合物,可以对抗癌活性进行更深入的研究,并对其他生物靶标进行调查。合成的衍生物含有重要的药效基团,具有在药物化学中应用的潜力。
{"title":"Ultrasound-Assisted, BF3·OEt2-Promoted, Multicomponent Synthesis of Chromene-Based Podophyllotoxin Analogues","authors":"RS Laurentiz, Fernanda A. Santos","doi":"10.1055/s-0043-1774865","DOIUrl":"https://doi.org/10.1055/s-0043-1774865","url":null,"abstract":"A novel method was developed to synthesise chromene-lactone analogues of podophyllotoxin using an ultrasound-assisted multicomponent reaction (MCR). The MCR involved tetronic acid, phenols, and aromatic aldehydes and was promoted by BF3·OEt2, resulting in the production of ten derivatives with different substituents on the aromatic rings in yields ranging from 32% to 93%. These compounds are of interest due to their reported activity against tumour cells. Their ease of synthesis through the MCR may allow for more in-depth studies on anticancer activity, as well as investigations of other biological targets. The synthesised derivatives contain important pharmacophoric groups for potential applications in medicinal chemistry.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140966740","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
Post-Ugi acid catalyzed fragmentation and trapping: An unprecedented approach towards novel bis(indolyl)acetamides 乌基酸后催化破碎和捕获:实现新型双(吲哚基)乙酰胺的前所未有的方法
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-15 DOI: 10.1055/a-2328-3091
Rinkal B Bhoraniya, Shiv Rohitbhai Desai, Mahesh Koladiya, Vidhi V Bhopekar, Swati H Patel, Sachin G Modha
A Post-Ugi Brønsted acid catalyzed unprecedented fragmentation followed by in situ trapping of the alkylideneindolenine intermediate by indole nucleophiles is developed to furnish novel bis(indolyl)acetamides. The amide fragment formed during this acid catalyzed fragmentation of Ugi adduct was also isolated and characterized. The carboxylic acid and amine components of Ugi reaction were smartly chosen to allow simple water wash for removal of amide fragment to obtain the desired bis(indolyl)acetamides in pure form.
研究人员开发了一种乌基后布氏酸催化的前所未有的碎裂方法,然后通过吲哚亲核剂对亚烷基吲哚啉中间体进行原位捕获,从而生成新型的双(吲哚基)乙酰胺。在这种酸催化的 Ugi 加合物破碎过程中形成的酰胺片段也被分离出来并进行了表征。巧妙地选择了 Ugi 反应中的羧酸和胺成分,以便通过简单的水洗去除酰胺片段,从而获得所需的纯双(吲哚基)乙酰胺。
{"title":"Post-Ugi acid catalyzed fragmentation and trapping: An unprecedented approach towards novel bis(indolyl)acetamides","authors":"Rinkal B Bhoraniya, Shiv Rohitbhai Desai, Mahesh Koladiya, Vidhi V Bhopekar, Swati H Patel, Sachin G Modha","doi":"10.1055/a-2328-3091","DOIUrl":"https://doi.org/10.1055/a-2328-3091","url":null,"abstract":"A Post-Ugi Brønsted acid catalyzed unprecedented fragmentation followed by in situ trapping of the alkylideneindolenine intermediate by indole nucleophiles is developed to furnish novel bis(indolyl)acetamides. The amide fragment formed during this acid catalyzed fragmentation of Ugi adduct was also isolated and characterized. The carboxylic acid and amine components of Ugi reaction were smartly chosen to allow simple water wash for removal of amide fragment to obtain the desired bis(indolyl)acetamides in pure form.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140976753","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
Silver-Mediated Homocoupling of Arylboronic Acids 银介导的芳硼酸同偶联反应
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-05-14 DOI: 10.1055/a-2315-8369
Tomoya Sakaguchi, Kyuta Fukuoka, Takuya Matsuki, Misa Kawase, Aya Tazawa, Yasuhiro Uozumi, Yoshimasa Matsumura, Osamu Shimomura, Atsushi Ohtaka

Here we describe a homocoupling reaction of arylboronic acid facilitated by silver carbonate, which proceeds smoothly in MeOH even at ambient temperature. The reaction exhibits broad functional group compatibility, affording a variety of symmetrical biaryls in satisfactory yields. Silver nanoparticles formed in situ serve as an accelerator in this process. Moreover, initial mechanistic investigations suggest that this transformation may occur via a radical mechanism.

在此,我们介绍了一种由碳酸银促进的芳基硼酸均偶联反应,该反应即使在环境温度下也能在 MeOH 中顺利进行。该反应具有广泛的官能团兼容性,能以令人满意的产率获得各种对称双芳基。在这一过程中,原位形成的银纳米粒子起到了加速器的作用。此外,初步的机理研究表明,这种转化可能是通过自由基机理发生的。
{"title":"Silver-Mediated Homocoupling of Arylboronic Acids","authors":"Tomoya Sakaguchi, Kyuta Fukuoka, Takuya Matsuki, Misa Kawase, Aya Tazawa, Yasuhiro Uozumi, Yoshimasa Matsumura, Osamu Shimomura, Atsushi Ohtaka","doi":"10.1055/a-2315-8369","DOIUrl":"https://doi.org/10.1055/a-2315-8369","url":null,"abstract":"<p>Here we describe a homocoupling reaction of arylboronic acid facilitated by silver carbonate, which proceeds smoothly in MeOH even at ambient temperature. The reaction exhibits broad functional group compatibility, affording a variety of symmetrical biaryls in satisfactory yields. Silver nanoparticles formed in situ serve as an accelerator in this process. Moreover, initial mechanistic investigations suggest that this transformation may occur via a radical mechanism.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141062056","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
期刊
Synlett
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1