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Ru-Mediated and Sulfur-Directed ortho-C–H Activation of Benzyl Thioethers with Internal Alkynes and Selective Hydrothiolation of Acetylene Dicarboxylates Ru 介导和硫引导的苄基硫醚与内部炔烃的正交-C-H 活化反应以及乙炔二羧酸盐的选择性氢硫化反应
Synthesis Pub Date : 2024-07-22 DOI: 10.1055/a-2348-7588
Sangeeta Kumari, Vijesh Tomar, Aditi Soni, Manisha Manisha, Charu Sharma, Raj K. Joshi
{"title":"Ru-Mediated and Sulfur-Directed ortho-C–H Activation of Benzyl Thioethers with Internal Alkynes and Selective Hydrothiolation of Acetylene Dicarboxylates","authors":"Sangeeta Kumari, Vijesh Tomar, Aditi Soni, Manisha Manisha, Charu Sharma, Raj K. Joshi","doi":"10.1055/a-2348-7588","DOIUrl":"https://doi.org/10.1055/a-2348-7588","url":null,"abstract":"<p>In this report, we have established a Ru(η<sup>6</sup>-C<sub>6</sub>H<sub>6</sub>)Cl<sub>2</sub> catalysed <i>ortho</i>-C–H activation of benzyl thioethers with alkynes under milder reaction conditions. The sulfur atom of benzyl thioethers worked as a directing group for <i>ortho</i>-C–H activation of benzyl thioethers. The reaction was found to tolerate a range of benzyl thioethers as well as alkynes. Moreover, the reaction is significantly influenced by the length of alkyl and aryl thioethers, with the best results being obtained with benzyl thioethers. Kinetic isotopic experiments suggest that the <i>ortho</i>-C–H bond-breaking is not a rate-determining step for the present reaction. In an unusual observation that has not been reported, apart from <i>ortho</i>-C–H activation, under the same reaction conditions, a selective debenzylative hydrothiolation was exclusively obtained with acrylates, which broadens the synthetic impact of benzyl thioethers for the preparation of mixed chalcogen ethers.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"63 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141782554","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Harnessing the Reactivity of ortho-Alkynylaldehydes: Silver Triflate Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules 利用原烷基醛的反应活性：三氟化银催化磷酰化荧光分子的区域选择性合成
Synthesis Pub Date : 2024-07-22 DOI: 10.1055/a-2356-8347
Deepika Thakur, Shivam A. Meena, Sushmita Sushmita, Akhilesh K. Verma
{"title":"Harnessing the Reactivity of ortho-Alkynylaldehydes: Silver Triflate Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules","authors":"Deepika Thakur, Shivam A. Meena, Sushmita Sushmita, Akhilesh K. Verma","doi":"10.1055/a-2356-8347","DOIUrl":"https://doi.org/10.1055/a-2356-8347","url":null,"abstract":"<p>An efficient approach for the facile synthesis of phosphonylated 1,3-dihydrofuro[3,4-<i>b</i>]quinolines and dihydrofuro[3,4-<i>b</i>]pyridines is developed. Reaction proceeds by the formation of new C–P and C–O bonds affording <i>Z</i>-selective phosphonylated products at room temperature. Diphenylphosphine oxides and dialkyl phosphites are explicitly incorporated into the carbonyl carbon of <i>o</i>-alkynylaldehydes in good to excellent yields. The reaction exhibits mild conditions, broad substrate scope, and the formation of three new bonds in the presence of a silver catalyst. The mechanistic studies revealed that the reaction proceeded <i>via</i> an ionic pathway in a 5-<i>exo</i>-dig manner to give <i>Z</i>-selective products, which was validated by X-ray crystallographic studies. Photophysical studies of selected compounds revealed the emission maxima in the range of 455 nm.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"254 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141782560","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Silylium-Ion-Initiated Twofold Halodealkylation of Fully Alkylated Silanes 硅鎓离子引发的全烷基化硅烷的双倍卤代烷基化反应
Synthesis Pub Date : 2024-07-19 DOI: 10.1055/a-2350-1323
Tobias Randt, Tao He, Hendrik F. T. Klare, Martin Oestreich
{"title":"Silylium-Ion-Initiated Twofold Halodealkylation of Fully Alkylated Silanes","authors":"Tobias Randt, Tao He, Hendrik F. T. Klare, Martin Oestreich","doi":"10.1055/a-2350-1323","DOIUrl":"https://doi.org/10.1055/a-2350-1323","url":null,"abstract":"<p>The synthesis of silanes starting from multifunctionalized precursors often suffers from low chemoselectivity due to the similar kinetic reaction profiles, leading to the formation of difficult to separate side products. The opposite approach, which is an access based on unreactive tetraalkylsilanes as starting materials, is far less developed. Making use of the silylium-ion-initiated chemoselective halodealkylation of tetraalkylsilanes recently developed by our laboratory, an extension of this protocol, namely the direct synthesis of dihalosilanes from tetraalkylsilanes, is reported. Following a sequence of halodehydrogenation and halodealkylation, trialkylhydrosilanes can also be converted into dihalosilanes. Commercially available 1,2-dihaloethane acts as the halogen source and is involved in the generation of the catalytically active arenium ion by an S<sub>E</sub>Ar substitution of the benzene solvent. The formation of an uncommon halogen-substituted silylium ion as an intermediate is assumed, likely accounting for the need of an elevated reaction temperature.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"29 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141741000","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Convenient One-Pot Process for Converting Thiols into Sulfonyl Fluorides Using H2O2 as an Oxidant 使用 H2O2 作为氧化剂将硫醇转化为磺酰氟的便捷式单锅工艺
Synthesis Pub Date : 2024-07-19 DOI: 10.1055/s-0043-1775384
Guang Tao, Eman Fayad, Ola A. Abu Ali, Bright Oyom, Hua-Li Qin
{"title":"A Convenient One-Pot Process for Converting Thiols into Sulfonyl Fluorides Using H2O2 as an Oxidant","authors":"Guang Tao, Eman Fayad, Ola A. Abu Ali, Bright Oyom, Hua-Li Qin","doi":"10.1055/s-0043-1775384","DOIUrl":"https://doi.org/10.1055/s-0043-1775384","url":null,"abstract":"<p>A novel protocol for synthesizing sulfonyl fluorides from thiols in one pot is reported. Utilizing SOCl<sub>2</sub> and H<sub>2</sub>O<sub>2</sub> as low-cost and convenient reagents allows the direct oxidative chlorination of readily available thiol derivatives to give the corresponding sulfonyl chlorides, with subsequent fluoride–chloride exchange mediated by KHF<sub>2</sub> giving access to the desired sulfonyl fluorides. This transformation features mild conditions, operational simplicity and high efficiency, and utilizes a broad substrate scope, including a variety of aryl, alkyl, benzyl and heteroaryl thiols.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"92 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141741179","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetyl­enedicarboxylates; Catalytic Hydrogenation of the Adducts α-羟基苄基膦酸盐与二烷基乙酰二羧酸盐的加成；加合物的催化加氢反应
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2352-7116
Mátyás Milen, Cintia Bese, Csenge Kovács, András Dancsó, György Keglevich
{"title":"The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetyl­enedicarboxylates; Catalytic Hydrogenation of the Adducts","authors":"Mátyás Milen, Cintia Bese, Csenge Kovács, András Dancsó, György Keglevich","doi":"10.1055/a-2352-7116","DOIUrl":"https://doi.org/10.1055/a-2352-7116","url":null,"abstract":"<p>α-Hydroxy-benzylphosphonates obtained by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites were added to the triple bond of dialkyl acetylenedicarboxylates. Optimum conditions involved a 24 hours stirring in the presence of 10% diazabicycloundecene in dichloromethane to afford the adducts as a mixture of predominant <i>E</i>- and a minor <i>Z</i>-isomers in 75–90% yields after flash chromatography. The structures of the geometrical isomers were confirmed by NOE- and ROE-measurements. Catalytic hydrogenation of the olefinic moiety of the adducts led to the diastereoisomers of corresponding saturated derivatives.</p>","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"53 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141740999","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Advances in the Synthesis of Bicyclo[3.1.1]heptanes 双环[3.1.1]庚烷合成的最新进展
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-2244
Jianyang Dong, Huijuan Liao, Dong Xue
{"title":"Recent Advances in the Synthesis of Bicyclo[3.1.1]heptanes","authors":"Jianyang Dong, Huijuan Liao, Dong Xue","doi":"10.1055/a-2367-2244","DOIUrl":"https://doi.org/10.1055/a-2367-2244","url":null,"abstract":"In the past three years, bicyclo[3.1.1]heptanes and their structural analogues have emerged as useful bioisosteres of meta-substituted (hetero)arenes. To meet increasing demand for bicyclo[3.1.1]heptanes, chemists have developed a plethora of novel methods for their synthesis. In this review, we assess research progress on their synthesis and functionalization, considering both scope and mechanism. In addition, we discuss the challenges posed by and outlook for the identification of novel reaction manifolds to access novel functionalized bicyclo[3.1.1]heptanes.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"63 21","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141643531","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Tactics and Strategies for the Synthesis of Cereblon Ligands 合成脑隆配体的策略和战略
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/s-0043-1775385
Elisia Villemure, Christian Nilewski, Yong Wang, Yuebiao Zhou, Alice R. Wong
{"title":"Tactics and Strategies for the Synthesis of Cereblon Ligands","authors":"Elisia Villemure, Christian Nilewski, Yong Wang, Yuebiao Zhou, Alice R. Wong","doi":"10.1055/s-0043-1775385","DOIUrl":"https://doi.org/10.1055/s-0043-1775385","url":null,"abstract":"Targeted protein degradation (TPD) has emerged as an important strategy to target disease-relevant proteins that were previously considered difficult to drug or even undruggable. Cereblon (CRBN) plays an outsized role in TPD as a preferred degradation-inducing effector protein for several reasons, including its anticipated broad protein substrate scope and its ligandability with drug-like small molecules. Notably, CRBN-based molecular glue degraders (MGDs) and proteolysis targeting chimeras (PROTACs) have shown success in clinical trials and, in some cases, as approved drugs. Thus, the interest in CRBN ligands within the pharmaceutical industry and academia has increased dramatically in recent years, highlighting the need for robust synthetic approaches towards them. This short review summarizes tactics and strategies to synthesize CRBN ligands, including the most recent developments in the field. Particular emphasis is put on the construction and direct functionalization of key CRBN binding motifs such as glutarimides and dihydrouracils.1 Introduction2 Cereblon Ligands with Glutarimide Binding Motif3 Cereblon Ligands with Dihydrouracil Binding Motif4 Cereblon Ligands with Other Binding Motifs5 Conclusions and Outlook","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"4 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141642607","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Design and Efficient Synthesis of New 4-Amino Substituted 2-(4-bromobenzyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines of Anticancer Interest and their In Silico Study 具有抗癌意义的新型 4-氨基取代 2-(4-溴苄基)-5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶的设计与高效合成及其硅学研究
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-1675
Sahil Arora, Shikha Thakur, V. Kaki, RAJ Kumar
{"title":"Design and Efficient Synthesis of New 4-Amino Substituted 2-(4-bromobenzyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines of Anticancer Interest and their In Silico Study","authors":"Sahil Arora, Shikha Thakur, V. Kaki, RAJ Kumar","doi":"10.1055/a-2367-1675","DOIUrl":"https://doi.org/10.1055/a-2367-1675","url":null,"abstract":"Thienopyrimidines are one of the emerging classes among fused pyrimidines owing to their broad spectrum of pharmacological properties, including antimicrobial, anti-inflammatory, antimalarial, anticancer, etc. The anticancer activity of these compounds is mechanistically proven via the inhibition of validated drug targets such as EGFR, VEGFR-2, PI3K, and c-kit. In this research article, we designed and attempted synthesis of new 4-amino substituted 2-(4-bromobenzyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines to explore their anticancer potential further. These heterocycles were designed based on pharmacophoric features of the core heterocycle, varying its C-4 substitution with a variety of amines and considering cancer protein-ligand interactions aiming to get potent lead molecules. The target compound-protein interaction complexes were analyzed, and lead compounds were identified based on their better binding affinity in molecular docking studies.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"75 12","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141643118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Simple Access to 3-(Hetero)arylated Derivatives of 2-Furoic Acid via Ru(II)-Catalyzed C3-H Arylation of 2-Furoylimidazole 通过 Ru(II)-Catalyzed C3-H Arylation of 2-Furoylimidazole 简单获得 3-(异)芳基化的 2-糠酸衍生物
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/s-0043-1775383
V. Chernyshev, Valentine P. Ananikov, K. Shepelenko, I. G. Gnatiuk, I. V. Lavrentev, M. E. Minyaev
{"title":"Simple Access to 3-(Hetero)arylated Derivatives of 2-Furoic Acid via Ru(II)-Catalyzed C3-H Arylation of 2-Furoylimidazole","authors":"V. Chernyshev, Valentine P. Ananikov, K. Shepelenko, I. G. Gnatiuk, I. V. Lavrentev, M. E. Minyaev","doi":"10.1055/s-0043-1775383","DOIUrl":"https://doi.org/10.1055/s-0043-1775383","url":null,"abstract":"A new approach for the preparation of a variety of 3-arylated 2-furoic acid derivatives has been developed. The approach involves selective Ru-catalyzed C3-H arylation of the furan moiety of readily available 2-furoyl-1-methylimidazole (using imidazole as a removable N-donor directing group), subsequent N-methylation, and nucleophilic substitution of the imidazole moiety with N, O, S, and C nucleophiles.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"5 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141641592","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Zinc Carbenoid-Promoted Methylene Insertion in Saturated Heterocycles: Mechanistic Insights and Reactivity Profiles 羰基化锌促进饱和杂环中的亚甲基插入：机理认识和反应性剖析
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/s-0043-1775381
Hiroyuki Nakamura, Masato Tsuda
{"title":"Zinc Carbenoid-Promoted Methylene Insertion in Saturated Heterocycles: Mechanistic Insights and Reactivity Profiles","authors":"Hiroyuki Nakamura, Masato Tsuda","doi":"10.1055/s-0043-1775381","DOIUrl":"https://doi.org/10.1055/s-0043-1775381","url":null,"abstract":"The ring expansion of saturated heterocycles through methylene insertion into N–O bonds using a zinc carbenoid is described. This transformation is applied to 1,2-oxazetidines and 1,2-oxazolidines, while N-tosylated 1,2-oxazinane affords a ring-opened product. Density functional theory calculations suggest a stepwise reaction mechanism of the ring expansion and elucidate the origins of the different reactivities observed.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"9 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141641294","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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