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Ni–H-Catalyzed Chemo- and Regioselective Hydroarylation of Vinylsilanes Ni-H 催化乙烯基硅烷的化学和区域选择性加氢反应
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-2434
Daniel Brösamlen, M. Oestreich
{"title":"Ni–H-Catalyzed Chemo- and Regioselective Hydroarylation of Vinylsilanes","authors":"Daniel Brösamlen, M. Oestreich","doi":"10.1055/a-2367-2434","DOIUrl":"https://doi.org/10.1055/a-2367-2434","url":null,"abstract":"A chemo- and regioselective hydroarylation of vinylsilanes with (hetero)aryl iodides under Ni–H catalysis is reported. This mild and straightforward protocol furnishes the anti-Markovnikov products in good yields as single regioisomers. This study demonstrates excellent control over the chemoselectivity and complements existing methods for the construction of the homobenzylic silanes.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"4 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141640200","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
Synthesis of N-Acyl-N’-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides 由磺酰基肼和活化酰胺合成 N-酰基-N'-磺酰基肼
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-2505
Yubin An, Jonghoon Oh, Sunwoo Lee
{"title":"Synthesis of N-Acyl-N’-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides","authors":"Yubin An, Jonghoon Oh, Sunwoo Lee","doi":"10.1055/a-2367-2505","DOIUrl":"https://doi.org/10.1055/a-2367-2505","url":null,"abstract":"A methodology was developed for synthesizing acyl sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base and 1,4-dioxane as a solvent at 25 °C for 12 h produced the highest yields. Among various amides tested, N-benzoylsuccinimide was found to be the most reactive, with reduced reactivity observed for N-mesityl, N-tosyl and N-Boc substituted tertiary benzoyl amides. Cross-reactions between a diverse range of N-benzoylsuccinimides and arylsulfonyl hydrazides successfully produced the corresponding N-acyl-N’-sulfonyl hydrazides with yields ranging from 63% to 93%.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"28 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141643874","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
Ring-closing metathesis as methodology for the synthesis of 2- and 3-arylbenzo[b]furans 作为 2-和 3-芳基苯并[b]呋喃合成方法的闭环偏析反应
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-2151
Melanie Visser, L. Twigge, C. Marais, B. Bezuidenhoudt
{"title":"Ring-closing metathesis as methodology for the synthesis of 2- and 3-arylbenzo[b]furans","authors":"Melanie Visser, L. Twigge, C. Marais, B. Bezuidenhoudt","doi":"10.1055/a-2367-2151","DOIUrl":"https://doi.org/10.1055/a-2367-2151","url":null,"abstract":"Olefin metathesis, which is well established in the petrochemical industry, is also emerging as a green technology in the manufacture of pharmaceutical and specialty chemicals. Arylbenzofurans are of interest for potential medicinal applications. In this paper we report on the synthesis of various 2-aryl- and 3-arylbenzo[b]furans with natural substitution patterns from readily available starting materials in a strategy that applies ring-closing metathesis with the Grubbs second generation catalyst as key step.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"12 10","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141641222","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
Synthesis and Aggregation-Induced Emission Properties of New Carbazole-Based Pyranones and their Ring Transformed Derivatives 新型咔唑基吡喃酮及其环变衍生物的合成与聚合诱导发射特性
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-1988
R. P. Vats, Priyanka Pandey, Shashwat Gupta, Suchitra Gupta, Shyamal Pal, Atul Goel
{"title":"Synthesis and Aggregation-Induced Emission Properties of New Carbazole-Based Pyranones and their Ring Transformed Derivatives","authors":"R. P. Vats, Priyanka Pandey, Shashwat Gupta, Suchitra Gupta, Shyamal Pal, Atul Goel","doi":"10.1055/a-2367-1988","DOIUrl":"https://doi.org/10.1055/a-2367-1988","url":null,"abstract":"A new series of N-phenyl-carbazole (N-phCbz) appended pyranones were designed and synthesized using α-oxo-ketene-S, S-acetal under mild reaction conditions in good yields. The reactivity of donor-acceptor (D-A)-based 2H-pyranones was utilised to develop their ring-transformed benzene-cored N-phenyl-carbazole derivatives. All the synthesised carbazole-based pyranones showed aggregation-induced emission (AIE) characteristics in 80-99% water fraction (fw) in DMSO. Among all the synthesized compounds, 6-(4-(9H-carbazol-9-yl)phenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile exhibited excellent AIE behaviour with ~70 fold increase in fluorescence in 80% fw at 550nm. Furthermore, this compound showed exceptionally high fluorescence in nonpolar solvent (THF) as compared to polar solvents like DMSO (~200-fold increase in fluorescence). The DFT, DSC and TGA analysis of the synthesised D--A compounds suggested the strong electron donor ability of N-phCbz, with good thermal stability in the range of 231-393 °C. These N-phenyl-carbazole-appended pyranones with interesting AIE properties have great potential as probes for bioimaging applications as well as for optoelectronic materials.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"19 12","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141641805","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
β-Nitroacrylates and Phenols as Key Precursors of Arenofuran-3-carboxylates 作为阿伦呋喃-3-羧酸盐关键前体的β-硝基丙烯酸酯和酚类化合物
Synthesis Pub Date : 2024-07-16 DOI: 10.1055/a-2367-1877
Benedetta Bassetti, Matteo Principi, R. Ballini, M. Petrini, A. Palmieri
{"title":"β-Nitroacrylates and Phenols as Key Precursors of Arenofuran-3-carboxylates","authors":"Benedetta Bassetti, Matteo Principi, R. Ballini, M. Petrini, A. Palmieri","doi":"10.1055/a-2367-1877","DOIUrl":"https://doi.org/10.1055/a-2367-1877","url":null,"abstract":"Herein we report a new practical and efficient preparation of benzofuran and naphthofuran-3-carboxylates starting from β-nitroacrylates and phenols. The reaction is promoted by indium trichloride and leads the target compounds from good to very good yields under microwave irradiations.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"8 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141644236","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
Iron(III)-Catalysed Povarov Cyclisation for the Synthesis of Fused Dibenzo[b,f][1,7]naphthyridine Embedded Arylpyrrolo Scaffolds 铁(III)催化的波瓦洛夫环化法合成嵌有芳基吡咯支架的融合二苯并[b,f][1,7]萘啶
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/a-2349-6836
Raj Kamal Sahoo, Gopal Rana, Abhishek Kar, Sourav Ghosh, Umasish Jana
{"title":"Iron(III)-Catalysed Povarov Cyclisation for the Synthesis of Fused Dibenzo[b,f][1,7]naphthyridine Embedded Arylpyrrolo Scaffolds","authors":"Raj Kamal Sahoo, Gopal Rana, Abhishek Kar, Sourav Ghosh, Umasish Jana","doi":"10.1055/a-2349-6836","DOIUrl":"https://doi.org/10.1055/a-2349-6836","url":null,"abstract":"<p>An FeCl<sub>3</sub>-catalyzed Povarov reaction for the efficient synthesis of dibenzo[<i>b</i>,<i>f</i>][1,7]naphthyridines utilizing 1-(2-alkynylaryl)-2-pyrrolecarbaldehydes and arylamines in excellent yields is demonstrated. The essential features of the present strategy are easy preparation of substrates, broad substrate scope, mild reaction conditions, and high atom economy and yields, in the presence of environmentally friendly iron catalysis.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"61 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141719021","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
Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols 可见光介导的重氮化合物与乙烯基锍酰化物和硫醇的双官能化作用
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/a-2350-1248
Srashti Bhardwaj, Raju Sen, Payel Adhikari, Janakiram Vaitla
{"title":"Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols","authors":"Srashti Bhardwaj, Raju Sen, Payel Adhikari, Janakiram Vaitla","doi":"10.1055/a-2350-1248","DOIUrl":"https://doi.org/10.1055/a-2350-1248","url":null,"abstract":"<p>A visible-light-induced multicomponent reaction of vinyl sulfoxonium ylide, thiol, and diazo ester to generate tertiary sulfide is described. The present diastereoselective <i>gem</i>-difunctionalization of the diazo ester can be achieved under mild conditions, as it does not require any additives, catalysts, or transition metals and is tolerant of air and moisture. Due to more nucleophilicity, vinyl sulfoxonium ylide undergoes S–H insertion with thiols to generate an allyl sulfide intermediate. Simultaneously, diazo ester undergoes photolysis to generate a carbene intermediate. Subsequently, the coupling of carbene and allyl sulfide intermediates generates sulfonium ylide, which undergoes Doyle–Kirmse rearrangement to generate tertiary sulfide scaffolds.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"30 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141719023","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
Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades 异氰基烯烃加成-环化-脱羧级联反应
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/s-0043-1774943
F. Fleming, John-Paul R Marrazzo, Tish Huynh
{"title":"Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades","authors":"F. Fleming, John-Paul R Marrazzo, Tish Huynh","doi":"10.1055/s-0043-1774943","DOIUrl":"https://doi.org/10.1055/s-0043-1774943","url":null,"abstract":"A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"41 24","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141645130","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
Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones N-Benzyl-propiolamides 的碘化制备，生成氮杂螺[5.5]十一烷三烯酮或苯并[c]氮杂卓酮
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/a-2349-6736
Chada Raji Reddy, Thallamapuram Nagendraprasad, Jannatul Islam, Uprety Ajaykumar, Cirandur Suresh Reddy, Srivari Chandrasekhar
{"title":"Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones","authors":"Chada Raji Reddy, Thallamapuram Nagendraprasad, Jannatul Islam, Uprety Ajaykumar, Cirandur Suresh Reddy, Srivari Chandrasekhar","doi":"10.1055/a-2349-6736","DOIUrl":"https://doi.org/10.1055/a-2349-6736","url":null,"abstract":"<p>Iodine-mediated oxidative annulations of <i>N</i>-benzyl-propiolamides are disclosed for the first time, providing either azaspiro[5.5]undecatrienones via dearomative <i>ipso</i>-annulation or benzo[<i>c</i>]azepinones through <i>ortho</i>-annulation. The selective construction of the aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substituents on the phenyl ring of the <i>N</i>-benzyl group.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"9 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141719022","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
Dehydration in Water: A Reagentless and Straightforward Synthesis of Tetrahydroquinazolines under Microwave Irradiation or by Stirring at Room Temperature, and Their Subsequent Conversion into Quinazolines in a Micellar Medium 水中脱水：微波辐照下或室温搅拌下四氢喹唑啉类化合物的无试剂直接合成及其在胶束介质中的后续喹唑啉类化合物转化
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/a-2348-5564
Padmini. C. Panjikar, Abigail. B. Pinheiro, Soumik Saha, Amrita Chatterjee, Mainak Banerjee
{"title":"Dehydration in Water: A Reagentless and Straightforward Synthesis of Tetrahydroquinazolines under Microwave Irradiation or by Stirring at Room Temperature, and Their Subsequent Conversion into Quinazolines in a Micellar Medium","authors":"Padmini. C. Panjikar, Abigail. B. Pinheiro, Soumik Saha, Amrita Chatterjee, Mainak Banerjee","doi":"10.1055/a-2348-5564","DOIUrl":"https://doi.org/10.1055/a-2348-5564","url":null,"abstract":"<p>Using a reagent- and catalyst-free approach, a series of 2-substituted 1,2,3,4-tetrahydroquinazolines is synthesized by cyclocondensation between aldehydes and 2-aminobenzylamines via dehydration in water. The reactions are complete in 2 minutes under microwave irradiation and proceed well under stirring at room temperature, affording tetrahydroquinazolines in high to excellent yields. The products are water-insoluble and are isolated by simple filtration, avoiding a conventional work-up step and offering an organic-solvent-free process. Furthermore, the tetrahydroquinazolines are efficiently oxidized in a micellar medium derived from cetyltrimethylammonium bromide (CTAB) using a cheap commercial bleaching solution (4% NaOCl in water) to give quinazolines in high yields. This sustainable protocol has a near zero E-factor.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"60 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141719024","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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