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Synthesis of 2H-azirine-2,2-dicarboxylic acids and their derivatives. 2h -氮嘧啶-2,2-二羧酸及其衍生物的合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-12-05 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.264
Anastasiya V Agafonova, Mikhail S Novikov, Alexander F Khlebnikov
{"title":"Synthesis of 2<i>H</i>-azirine-2,2-dicarboxylic acids and their derivatives.","authors":"Anastasiya V Agafonova, Mikhail S Novikov, Alexander F Khlebnikov","doi":"10.3762/bjoc.20.264","DOIUrl":"10.3762/bjoc.20.264","url":null,"abstract":"<p><p>Methods for the preparation of 3-aryl-2<i>H</i>-azirine-2,2-dicarboxylic acids and their amides, esters, and azides by FeCl<sub>2</sub>-catalyzed isomerization of 3-aryl-5-chloroisoxazole-4-carbonyl chlorides into 3-aryl-2<i>H</i>-azirine-2,2-dicarbonyl dichlorides followed by their reaction with nucleophiles are reported. Two approaches to the preparation of 3-aryl-5-chloroisoxazole-4-carbonyl chlorides have been developed.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3191-3197"},"PeriodicalIF":2.2,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11635289/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142817096","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
Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling. Germanyl三唑作为CuAAC多样化和化学选择性正交交叉偶联的平台。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-12-05 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.265
John M Halford-McGuff, Thomas M Richardson, Aidan P McKay, Frederik Peschke, Glenn A Burley, Allan J B Watson
{"title":"Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling.","authors":"John M Halford-McGuff, Thomas M Richardson, Aidan P McKay, Frederik Peschke, Glenn A Burley, Allan J B Watson","doi":"10.3762/bjoc.20.265","DOIUrl":"10.3762/bjoc.20.265","url":null,"abstract":"<p><p>We report the synthesis of germanyl triazoles formed via a copper-catalysed azide-alkyne cycloaddition (CuAAC) of germanyl alkynes. The reaction is often high yielding, functional group tolerant, and compatible with complex molecules. The installation of the Ge moiety enables further diversification of the triazole products, including chemoselective transition metal-catalysed cross-coupling reactions using bifunctional boryl/germyl species.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3198-3204"},"PeriodicalIF":2.2,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11635283/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816929","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
Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold. 基于四氢哒嗪支架的扩展氟化三肽的合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-12-04 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.262
Thierry Milcent, Pascal Retailleau, Benoit Crousse, Sandrine Ongeri
{"title":"Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold.","authors":"Thierry Milcent, Pascal Retailleau, Benoit Crousse, Sandrine Ongeri","doi":"10.3762/bjoc.20.262","DOIUrl":"10.3762/bjoc.20.262","url":null,"abstract":"<p><p>The synthesis of tripeptides incorporating new fluorinated heterocyclic hydrazino acids, based on the tetrahydropyridazine scaffold is described. Starting from simple fluorinated hydrazones, these non-proteinogenic cyclic β-amino acids were easily prepared by a zinc-catalyzed aza-Barbier reaction followed by an intramolecular Michael addition. Preliminary conformational studies on tripeptides including this scaffold in the central position show an extended conformation in solution (NMR) and in the solid state (X-ray).</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3174-3181"},"PeriodicalIF":2.2,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11635284/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142817097","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
Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds. 用高价碘化合物直接三氟化羰基亚砜酰化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-12-04 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.263
Radell Echemendía, Carlee A Montgomery, Fabio Cuzzucoli, Antonio C B Burtoloso, Graham K Murphy
{"title":"Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds.","authors":"Radell Echemendía, Carlee A Montgomery, Fabio Cuzzucoli, Antonio C B Burtoloso, Graham K Murphy","doi":"10.3762/bjoc.20.263","DOIUrl":"10.3762/bjoc.20.263","url":null,"abstract":"<p><p>A novel study on the hypervalent iodine-mediated polyfluoroalkylation of sulfoxonium ylides was developed. Sulfoxonium ylides, known for their versatility and stability, are promising substrates for numerous transformations in synthetic chemistry. This report demonstrates the successful derivatization of sulfoxonium ylides with trifluoroethyl or tetrafluoropropyl groups, and provides valuable insights into the scope and limitations of this approach. Nineteen examples have been prepared (45-92% yields), with structural diversity modified at two key sites on the sulfoxonium ylide reactants. Finally, DFT calculations provided insights about the mechanism of this transformation, which strongly suggest that an S<sub>N</sub>2 reaction is operative.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3182-3190"},"PeriodicalIF":2.2,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11635294/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816925","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
Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies. 多组分反应驱动发现和优化靶向中枢神经系统病变的药物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-12-03 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.261
Lucía Campos-Prieto, Aitor García-Rey, Eddy Sotelo, Ana Mallo-Abreu
{"title":"Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies.","authors":"Lucía Campos-Prieto, Aitor García-Rey, Eddy Sotelo, Ana Mallo-Abreu","doi":"10.3762/bjoc.20.261","DOIUrl":"10.3762/bjoc.20.261","url":null,"abstract":"<p><p>The ongoing quest to discover effective treatments for diseases remains a significant challenge for the scientific community. Multicomponent reactions (MCRs) have emerged as powerful tools in accelerating drug discovery, enabling the rapid generation of chemical libraries with high diversity in a time-efficient and environmentally sustainable manner. In this review, we focus on central nervous system (CNS) disorders, particularly Alzheimer's disease, Parkinson's disease, schizophrenia, depression, and epilepsy, where MCRs have contributed to the development of promising ligands in recent years. Rather than providing an exhaustive overview, this review aims to highlight key studies that address major CNS pathologies, relevant drug targets, and various MCR approaches. We have carefully selected representative articles and apologize to the authors whose important contributions may not be included. By concentrating on these pivotal studies, we strive to offer a clear and concise perspective on current research trends and breakthroughs in this field.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3151-3173"},"PeriodicalIF":2.2,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11635293/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142817094","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
Surprising acidity for the methylene of 1,3-indenocorannulenes? 令人惊讶的1,3-吲哚环烯亚甲基的酸度？
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-12-02 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.260
Shi Liu, Märt Lõkov, Sofja Tshepelevitsh, Ivo Leito, Kim K Baldridge, Jay S Siegel
{"title":"Surprising acidity for the methylene of 1,3-indenocorannulenes?","authors":"Shi Liu, Märt Lõkov, Sofja Tshepelevitsh, Ivo Leito, Kim K Baldridge, Jay S Siegel","doi":"10.3762/bjoc.20.260","DOIUrl":"10.3762/bjoc.20.260","url":null,"abstract":"<p><p>Quantitative assessment of the first acidity constant (p<i>K</i> <sub>a</sub>) for BFC (27.6 in CH<sub>3</sub>CN) and FIC (27.8 in CH<sub>3</sub>CN) shows the methylene protons to be significantly more acidic than those in related cyclopentadiene (32 in CH<sub>3</sub>CN), indene (34 in CH<sub>3</sub>CN), or fluorene (37 in CH<sub>3</sub>CN) and comparable to the methine of 9-perfluorophenylfluorene (28.14 in CH<sub>3</sub>CN). This work reports quantitative p<i>K</i> <sub>a</sub> values of BFC and FIC, places those values in a broadened context of CpH-cognate hydrocarbon acidity and presents a Clar-Loschmidt graph perspective to help understand the \"surprises\".</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3144-3150"},"PeriodicalIF":2.2,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11635290/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142817095","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
Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF5- and CF3SF4-containing [2]staffanes. 通过自由基极性匹配控制[1.1.1]推进剂的低聚化：含SF5-和cf3sf4的[2]烷的选择性合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-29 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.259
Jón Atiba Buldt, Wang-Yeuk Kong, Yannick Kraemer, Masiel M Belsuzarri, Ansh Hiten Patel, James C Fettinger, Dean J Tantillo, Cody Ross Pitts
{"title":"Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF<sub>5</sub>- and CF<sub>3</sub>SF<sub>4</sub>-containing [2]staffanes.","authors":"Jón Atiba Buldt, Wang-Yeuk Kong, Yannick Kraemer, Masiel M Belsuzarri, Ansh Hiten Patel, James C Fettinger, Dean J Tantillo, Cody Ross Pitts","doi":"10.3762/bjoc.20.259","DOIUrl":"https://doi.org/10.3762/bjoc.20.259","url":null,"abstract":"<p><p>Selectivity in radical chain oligomerizations involving [1.1.1]propellane - i.e., to make [<i>n</i>]staffanes - has been notoriously challenging to control when <i>n</i> > 1 is desired. Herein, we report selective syntheses of SF<sub>5</sub>- and CF<sub>3</sub>SF<sub>4</sub>-containing [2]staffanes from SF<sub>5</sub>Cl and CF<sub>3</sub>SF<sub>4</sub>Cl, demonstrating cases whereby oligomerization is preferentially truncated after incorporation of two bicyclopentane (BCP) units. Synthetic and computational studies suggest this phenomenon can be attributed to alternating radical polarity matching. In addition, single-crystal X-ray diffraction (SC-XRD) data reveal structurally interesting features of the CF<sub>3</sub>SF<sub>4</sub>-containing [2]staffane in the solid state.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3134-3143"},"PeriodicalIF":2.2,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11610489/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142765999","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
Hypervalent iodine-mediated intramolecular alkene halocyclisation. 高价碘介导的分子内烯烃卤环化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-28 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.258
Charu Bansal, Oliver Ruggles, Albert C Rowett, Alastair J J Lennox
{"title":"Hypervalent iodine-mediated intramolecular alkene halocyclisation.","authors":"Charu Bansal, Oliver Ruggles, Albert C Rowett, Alastair J J Lennox","doi":"10.3762/bjoc.20.258","DOIUrl":"https://doi.org/10.3762/bjoc.20.258","url":null,"abstract":"<p><p>The chemistry of hypervalent iodine (HVI) reagents has gathered increased attention towards the synthesis of a wide range of chemical structures. HVI reagents are characterized by their diverse reactivity as oxidants and electrophilic reagents. In addition, they are inexpensive, non-toxic and considered to be environmentally friendly. An important application of HVI reagents is the synthesis of halogenated cyclic compounds, in particular, the intramolecular HVI-mediated halocyclisation of alkenes using carbon, oxygen, nitrogen or sulfur nucleophiles. Herein, we describe the examples reported in the literature, which are organised by the different halogens involved and the internal nucleophiles.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3113-3133"},"PeriodicalIF":2.2,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11610491/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142766029","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
Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts. 无金属四吡咯大环催化剂的研究进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-27 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.257
Mandeep K Chahal
{"title":"Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts.","authors":"Mandeep K Chahal","doi":"10.3762/bjoc.20.257","DOIUrl":"https://doi.org/10.3762/bjoc.20.257","url":null,"abstract":"<p><p>This review provides an overview of recent progress made in the field of catalysis using metal-free tetrapyrrolic macrocycles, focusing on calix[4]pyrroles, porphyrins and corroles, which are structurally related to porphyrins. Calix[4]pyrroles are versatile receptors in supramolecular chemistry while porphyrins are considered as 'pigment of life' due to their role in vital biological processes. Beyond their natural functions, synthetic porphyrins have been applied in various fields, including organometallic catalysis, dye-sensitized solar cells, sensing, artificial olfactory systems, photodynamic therapy (PDT), anticancer drugs, biochemical probes, and electrochemical devices. Relevant examples of these two pyrrolic macrocycles as metal-free organocatalysts, photocatalysts, and electrocatalysts are presented here. The effect of macrocyclic structural modifications such as their functionalization with different substituents, distortion from planarity, conformational flexibility and rigidity towards catalytic activity are presented, highlighting the potential of these two macrocycles as metal-free catalysts.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3085-3112"},"PeriodicalIF":2.2,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11610490/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142765997","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
Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction. 高阶多组分反应合成1,5-二取代四唑-甲磺酰吲哚杂化体系。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-26 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.256
Cesia M Aguilar-Morales, América A Frías-López, Nadia V Emilio-Velázquez, Alejandro Islas-Jácome, Angelica Judith Granados-López, Jorge Gustavo Araujo-Huitrado, Yamilé López-Hernández, Hiram Hernández-López, Luis Chacón-García, Jesús Adrián López, Carlos Jesús Cortés-García
{"title":"Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction.","authors":"Cesia M Aguilar-Morales, América A Frías-López, Nadia V Emilio-Velázquez, Alejandro Islas-Jácome, Angelica Judith Granados-López, Jorge Gustavo Araujo-Huitrado, Yamilé López-Hernández, Hiram Hernández-López, Luis Chacón-García, Jesús Adrián López, Carlos Jesús Cortés-García","doi":"10.3762/bjoc.20.256","DOIUrl":"https://doi.org/10.3762/bjoc.20.256","url":null,"abstract":"<p><p>A series of 1,5-disubstituted tetrazole-indole hybrids were synthesized via a high-order multicomponent reaction consisting of an Ugi-azide/Pd/Cu-catalyzed hetero-annulation cascade sequence. This operationally simple one-pot protocol allowed high bond-forming efficiency and creating six new bonds (two C-C, three C-N, and one N-N). Additionally, the products were evaluated against breast cancer MCF-7 cells, finding moderate activity in the compounds substituted with fluorine and chlorine.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3077-3084"},"PeriodicalIF":2.2,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11610483/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142766032","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
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