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Synthesis of N-Acylsulfenamides from Amides and N-Thiosuccinimides. 从酰胺和 N-硫代丁二酰亚胺合成 N-酰基亚磺酰胺。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2023-08-01 Epub Date: 2022-12-20 DOI: 10.1055/s-0041-1738430
Jessica T Liu, Daniel S Brandes, Nathaniel S Greenwood, Jonathan A Ellman
{"title":"Synthesis of <i>N</i>-Acylsulfenamides from Amides and <i>N</i>-Thiosuccinimides.","authors":"Jessica T Liu, Daniel S Brandes, Nathaniel S Greenwood, Jonathan A Ellman","doi":"10.1055/s-0041-1738430","DOIUrl":"10.1055/s-0041-1738430","url":null,"abstract":"<p><p>Herein is reported a robust and general method for the preparation of <i>N</i>-acylsulfenamides, important functionalities that have recently been utilized as central inputs for the asymmetric synthesis of high oxidation state sulfur compounds. This straightforward transformation proceeds by reaction of primary amides, carbamates, sulfonamides, sulfinamides, and ureas with stable <i>N</i>-thiosuccinimides or <i>N</i>-thiophthalimides, which in turn are prepared in a single step from commercial thiols. The use of stable <i>N</i>-thiosuccinimide and <i>N</i>-thiophthalimide reactants is desirable because it obviates the use of highly reactive sulfenyl chlorides.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10348737/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9830912","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Efficient Synthesis of Chirally Enriched 1 H -Imidazo[1,2- b ]pyrazole- and 4 H -Imidazo[1,2- b ][1,2,4]triazole-Based Bioactive Glycohybrids 高效合成手性富集的1 H -咪唑[1,2- b]吡唑和4 H -咪唑[1,2- b][1,2,4]三唑类生物活性糖杂化合物
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-31 DOI: 10.1055/a-2157-9100
Vinay Kumar Mishra, Ghanshyam Tiwari, A. Khanna, Rajdeep Tyagi, R. Sagar
{"title":"Efficient Synthesis of Chirally Enriched 1 H -Imidazo[1,2- b ]pyrazole- and 4 H -Imidazo[1,2- b ][1,2,4]triazole-Based Bioactive Glycohybrids","authors":"Vinay Kumar Mishra, Ghanshyam Tiwari, A. Khanna, Rajdeep Tyagi, R. Sagar","doi":"10.1055/a-2157-9100","DOIUrl":"https://doi.org/10.1055/a-2157-9100","url":null,"abstract":"Carbohydrates, traditionally known for their energy-providing role, have gained significant attention in drug discovery due to their diverse bioactivities and stereodiversity. However, pure carbohydrate molecules often exhibit limited bioactivity and suboptimal chemical and physical characteristics. To address these challenges, bioactive scaffolds have been incorporated into carbohydrate to enhance their bioactivity and improve their overall properties. Among the various heterocyclic structural motifs known for their pharmacological properties, imidazo-pyrazole and imidazo-triazole skeleton have gained larger attention among synthetic and medicinal chemists as they possess good biological and pharmacological properties. Present work deals with the incorporation of carbohydrate moieties into these bioactive scaffolds (imidazo-pyrazole and imidazo-triazole skelton) to develop an efficient synthetic protocol for new class of imidazo-pyrazole and imidazo-triazole glycohybrid molecules. The carbohydrate derived α-iodo-2,3-dihydro-4H-pyran-4-ones have been identified as suitable precursors which were coupled with various amino-pyrazoles and amino-triazoles to obtain designed glycohybrids. Thus, various imidazo-pyrazole and imidazo-triazole based glycohybrids have been prepared efficiently in good to very good yield. These new glycohybrids evaluated for their anticancer activity and selected compounds were found to possess submicromolar anticancer activity. These molecules could potentially be developed as new chemical entities and may encourage the use of carbohydrates in stereo-divergent synthesis and drug discovery processes.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85945589","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
Progress on the Enantioselective Synthesis of Axially Chiral Cycloalkylidenes 轴向手性环烷基烯的对映选择性合成研究进展
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-24 DOI: 10.1055/a-2159-1688
Zi-Lu Wang, Yun‐He Xu
{"title":"Progress on the Enantioselective Synthesis of Axially Chiral Cycloalkylidenes","authors":"Zi-Lu Wang, Yun‐He Xu","doi":"10.1055/a-2159-1688","DOIUrl":"https://doi.org/10.1055/a-2159-1688","url":null,"abstract":"The discovery of new asymmetric synthetic methodologies and the asymmetric synthesis of new chiral compounds have been the central work of synthetic organic chemists for decades. Axially chiral compounds have gained considerable attention in recent years because of their unique utility in asymmetric catalysis and synthesis. The asymmetric synthesis of axially chiral cycloalkylidenes, a subset of axial chirality molecules, is sluggish compared to chiral allenes, and chiral biaryl compounds. In this review, different approaches for the synthesis of axially chiral cycloalkylidenes are summarized.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83010977","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
Recent Advances on High-Order Dipolar Annulations of Donor–Acceptor Cyclopropanes/Cyclobutanes 供体-受体环丙烷/环丁烷高阶偶极环的研究进展
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-21 DOI: 10.1055/a-2155-3615
Liangliang Yang, Haiyang Wang, Ming Lang, Shiyong Peng
{"title":"Recent Advances on High-Order Dipolar Annulations of Donor–Acceptor Cyclopropanes/Cyclobutanes","authors":"Liangliang Yang, Haiyang Wang, Ming Lang, Shiyong Peng","doi":"10.1055/a-2155-3615","DOIUrl":"https://doi.org/10.1055/a-2155-3615","url":null,"abstract":"This short review summarizes the recent impressive developments in the high-order dipolar annulations (HODAs) of donor–acceptor cyclopropanes (DACs) and donor–acceptor cyclobutanes (DABs) to afford medium-sized (hetero)cycles.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81739678","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 Pyrido[2,3- d ]pyrimidines Catalyzed by 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/ tert -Butyl Nitrite (TBN)/O 2 2,3-二氯-5,6-二氰-1,4-苯醌(DDQ)/叔丁基亚硝酸盐(TBN)/ o2催化合成吡啶[2,3- d]嘧啶
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-19 DOI: 10.1055/a-2156-7470
Dongping Cheng, Hongshuang Xia, Huafang Gu, Yawei Wang, Jinghua Li, Xiaoliang Xu
{"title":"Synthesis of Pyrido[2,3- d ]pyrimidines Catalyzed by 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/ tert -Butyl Nitrite (TBN)/O 2","authors":"Dongping Cheng, Hongshuang Xia, Huafang Gu, Yawei Wang, Jinghua Li, Xiaoliang Xu","doi":"10.1055/a-2156-7470","DOIUrl":"https://doi.org/10.1055/a-2156-7470","url":null,"abstract":"Catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-butyl nitrite (TBN)/O2, an efficient tandem oxidative reaction of uracils/thiouracil with 1,3-diarylpropenes is disclosed. It undergoes oxidative coupling, intramolecular cyclization, and dehydro-aromatization to provide multi-substituted pyrido[2,3-d]pyrimidines/thiopyrido[2,3-d]pyrimidines in moderate to excellent yields. It has the advantages of high atom economy, green terminal oxidant, and metal-free conditions.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79334014","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
Recent Developments on the Synthesis of Sulfoxides via Sulfenate Anions 硫酸盐阴离子法合成亚砜的研究进展
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-18 DOI: 10.1055/a-2155-3498
Fumito Saito
{"title":"Recent Developments on the Synthesis of Sulfoxides via Sulfenate Anions","authors":"Fumito Saito","doi":"10.1055/a-2155-3498","DOIUrl":"https://doi.org/10.1055/a-2155-3498","url":null,"abstract":"Since the early 2000s, novel synthetic methods for the preparation of sulfoxides have emerged that involve sulfenate anions as sulfur nucleophiles. This short review showcases key advances in these sulfenate protocols, including catalytic enantioselective alkylation and arylation, and provides future directions for this research field.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87435116","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
SYNFORM ISSUE 2023/8 Synform issue 2023/8
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-17 DOI: 10.1055/s-0040-1720605
M. Zanda
{"title":"SYNFORM ISSUE 2023/8","authors":"M. Zanda","doi":"10.1055/s-0040-1720605","DOIUrl":"https://doi.org/10.1055/s-0040-1720605","url":null,"abstract":"using thioanisole and p -toluenesulfonamide as test substrates. Indeed, selective formation of the sulfilimine was observed when bromide was used as the mediator and MeOH as the base. In addition, bromide and MeOH also served as supporting electrolyte and solvent, which allowed for an extremely efficient use of the reactants.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84443103","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
Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5- b ]indoles and Related Heterocycles 2-(三氯甲基)-5-苯基嘧啶的硝基环化:在2-(三氯甲基)嘧啶[4,5- b]吲哚及相关杂环合成中的应用
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-14 DOI: 10.1055/a-2159-1611
Ulises Jose Vargas-Cruz, José G. Peralta-Chávez, Misael A. Romero-Reyes, D. Martínez-Otero, M. Romero-Ortega
{"title":"Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5- b ]indoles and Related Heterocycles","authors":"Ulises Jose Vargas-Cruz, José G. Peralta-Chávez, Misael A. Romero-Reyes, D. Martínez-Otero, M. Romero-Ortega","doi":"10.1055/a-2159-1611","DOIUrl":"https://doi.org/10.1055/a-2159-1611","url":null,"abstract":"An aromatic C–H nitrene insertion of 2-trichloromethylpyrimidines bearing a phenyl substituent in C-5 position is described. Treatment of 2-trichloromethyl-4-chloro-5-phenylpyrimidines with sodium azide in DMF or the reflux of 2-trichloromethyl-4-azido-5-phenylpyrimidines in toluene provided 2-trichloromethylpyrimido[4,5-b]indole derivatives in moderate yields. Excellent yields of this heterocyclic systems were obtained through of the aromatic C–H insertion with Du Bois catalyst. This is an attractive approach for synthesizing pyrimido[4,5-b]indoles with a trichloromethyl substituent in the pyrimidine moiety.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84105050","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
New Route to Direct Synthesis of Symmetrical Ureas from Carboxylic Acids 羧酸直接合成对称脲的新途径
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-13 DOI: 10.1055/a-2172-8329
Daniel Jahani, H. Yassine, Mostafa Khouili, M. D. Pujol
{"title":"New Route to Direct Synthesis of Symmetrical Ureas from Carboxylic Acids","authors":"Daniel Jahani, H. Yassine, Mostafa Khouili, M. D. Pujol","doi":"10.1055/a-2172-8329","DOIUrl":"https://doi.org/10.1055/a-2172-8329","url":null,"abstract":"ABSTRACT: The first method for the direct conversion of carboxylic acids into ureas has been developed. The classical procedures described above for the formation of ureas from carboxylic acids require two steps, preparation of the isocyanate followed by its aminolysis. In this work, arylcarboxylic and arylalkylcarboxylic acids have been transformed into symmetric ureas in a single step using DPPA or sodium azide as nitrogen source. The addition of water (method A) or the presence of solvent water (method B) was essential for the formation of symmetrical ureas from the corresponding carboxylic acids. The corresponding ureas have been obtained in good to excellent yields of 46 to 100%. This procedure was compatible with differ-ent substituents present in the starting carboxylic acid.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76495965","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
Zinc-Mediated C–H Metalations in Modern Organic Synthesis 现代有机合成中锌介导的C-H金属化
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-07-10 DOI: 10.1055/a-2155-3423
Daria Karolina Wanic, Rebecca Melvin, G. Barker
{"title":"Zinc-Mediated C–H Metalations in Modern Organic Synthesis","authors":"Daria Karolina Wanic, Rebecca Melvin, G. Barker","doi":"10.1055/a-2155-3423","DOIUrl":"https://doi.org/10.1055/a-2155-3423","url":null,"abstract":"C-H deprotometalations have long occupied a key role in modern organic synthesis in both the research laboratory and pharmaceutical and fine chemical manufacture, thanks to readily accessible reagents and well-established procedures. Typically, organolithiums are the reagent of choice thanks to high reactivity and ease of use but these are incompatible with base- and nucleophile-sensitive functional groups. In comparison, organozinc base complexes offer a milder approach to deprotonative C-H functionalisations, and compatibility with a wide range of functionalities which would be problematic when using the alternative organolithium or organomagnesium reagents has now been demonstrated. Here, we review the current state of the art in zinc-mediated C-H metalations at substituted arenes, heteroarenes and Csp3-H sites.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82193134","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
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