Joaquín Marchán-García, Marcos J. Lo Fiego, Yanina Moglie
{"title":"Selective Carbohydrate Deacetylation: Simple and Mild Approach based on Supported Copper Nanoparticles","authors":"Joaquín Marchán-García, Marcos J. Lo Fiego, Yanina Moglie","doi":"10.1002/hlca.202400120","DOIUrl":"https://doi.org/10.1002/hlca.202400120","url":null,"abstract":"<p>Herein, a selective protocol for the complete removal of acetyl protecting groups from carbohydrate derivatives based on copper nanoparticles supported on activated carbon is presented. The deacetylation procedure occurs under neutral conditions, is applicable to a wide range of substrates and tolerates a variety of functional groups (e. g. azido, allyl and silyl groups). Quantitative yields of the deacetylated product were obtained for all evaluated derivatives using catalyst amounts between 1 and 10 mol%. As a special highlight, the dual behavior of the nanocatalyst in both deacetylation and click reactions is reported.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142540894","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}
{"title":"Sascha Hoogendoorn","authors":"","doi":"10.1002/hlca.202400123","DOIUrl":"https://doi.org/10.1002/hlca.202400123","url":null,"abstract":"<p>Young people should study chemistry because it's both fun and useful. I chose my field of research because I love to be able to make precision tools using chemistry to gain understanding of, and control over, a biological system. My valuable advice from a more senior colleague at the beginning of my career was ‘a scientific path is not linear, even though it may appear to be so when the story is told afterwards'\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400123","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142540878","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}
Rahul Giri, Mathias Kissling, Egor Zhilin, Anthony J. Fernandes, Quentin E. L. Ordan, Dmitry Katayev
{"title":"Divergent Synthesis of Trifluoromethyl Ketones via Photoredox Activation of Halotrifluoroacetones","authors":"Rahul Giri, Mathias Kissling, Egor Zhilin, Anthony J. Fernandes, Quentin E. L. Ordan, Dmitry Katayev","doi":"10.1002/hlca.202400125","DOIUrl":"https://doi.org/10.1002/hlca.202400125","url":null,"abstract":"<p>Fluorine's high electronegativity, lipophilicity, and metabolic stability make it a valuable element for drug design and development. Consequently, significant synthetic efforts have focused on introducing fluorine and fluorinated motifs into organic molecules, with the synthesis of trifluoromethyl ketones (TFMKs) recently attracting considerable attention. Building on our ongoing research on radical organofluorine chemistry, we present herein the divergent synthesis of trifluoromethyl ketones directly from olefins using readily available chloro- and bromotrifluoroacetone as synthetic precursors of the trifluoroacetonyl radical under photoredox catalysis. Mechanistic studies revealed that the divergence is attained through radical polar crossover (RPC) and hydrogen atom transfer (HAT) mechanisms.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400125","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142540850","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}
Hao Jiang, Bin Wu, Dominik Rufle, Liping Wang, Min Shi, Michael Parmentier, Fabrice Gallou
{"title":"Micelle Enabled Buchwald-Hartwig Amination in Water with the Bening by Design Surfactant TPGS-750-M for the Synthesis of the JAK Inhibitor 4-((2-Chlorophenyl)amino)-6-((6-methylpyridin-2-yl)amino)nicotinamide","authors":"Hao Jiang, Bin Wu, Dominik Rufle, Liping Wang, Min Shi, Michael Parmentier, Fabrice Gallou","doi":"10.1002/hlca.202400094","DOIUrl":"10.1002/hlca.202400094","url":null,"abstract":"<p>An efficient and scalable Buchwald-Hartwig amination towards the synthesis of the API candidate 4-((2-Chlorophenyl)amino)-6-((6-methylpyridin-2-yl)amino)nicotinamide as a JAK inhibitor was described. The process was developed using water and a water-miscible co-solvent. It was facilitated by the benign by design surfactant TPGS-750-M, that promoted the robust and reliable preparation of our target compound in high yields, with improved reaction profile and via an operationally simple protocol.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141930096","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}
Akanksha Keshri, Anjali Gupta, Upma Gulati, Tara Datt Bhatt, Maneesh Kashyap, Joydev K. Laha
{"title":"A Telescopic, Scalable and Industrially Feasible Method for the Synthesis of Antidepressant Drug, Moclobemide","authors":"Akanksha Keshri, Anjali Gupta, Upma Gulati, Tara Datt Bhatt, Maneesh Kashyap, Joydev K. Laha","doi":"10.1002/hlca.202400075","DOIUrl":"10.1002/hlca.202400075","url":null,"abstract":"<p>An improved, scalable, industrially feasible telescopic process for multigram synthesis of highly commercialized antidepressant drug, moclobemide has been developed. Unlike the conventional approaches, this process enjoys the privilege of being an economical, operationally simple, effectively scalable, and quantitative method for the synthesis of amide-containing drug moclobemide, showcasing easy isolation and purification without the aid of column chromatography. An environmentally benign reagent combination of TBN and NHS very effectively converts the acyl source, 4-chlorobenzaldehyde into its <i>N</i>-hydroxysuccinimide ester intermediate, which simply affords the drug molecule after nucleophilic substitution with the amine source. The synthetic process has successfully been scaled-up upto ~145 g scale with 75 % overall yield and >95 % first crop HPLC purity.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141642620","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}
Dr. Karri Raghavulu, Varukolu Shanker, Dr. Ramakrishna Gudipati, Prof. Dr. Keloth Basavaiah, Dr. Raju Doddipalla, Dr. Mahipal Yadav, Dr. Satyanarayana Yennam, Dr. Manoranjan Behera
{"title":"Conversion of Isoxazoles to Functionalized Pyrrole and Isoquinoline Derivatives via ROCC Mechanism","authors":"Dr. Karri Raghavulu, Varukolu Shanker, Dr. Ramakrishna Gudipati, Prof. Dr. Keloth Basavaiah, Dr. Raju Doddipalla, Dr. Mahipal Yadav, Dr. Satyanarayana Yennam, Dr. Manoranjan Behera","doi":"10.1002/hlca.202400057","DOIUrl":"10.1002/hlca.202400057","url":null,"abstract":"<p>Herein, we report a new method for the synthesis of functionalized pyrrole and isoquinoline derivatives using isoxazole based precursors. The reaction proceeds through the ring opening and ring closing cascade mechanism (ROCC) to afford pyrrole or isoquinoline derivatives in good to excellent yields under very mild experimental conditions. Product outcome relies on the strategic placement of different substituents on the isoxazole moiety. The present method is also applicable to synthesize functionalized isoquinolone derivatives.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141645339","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}