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Synthesis of Spin-Labeled α-/β-Galactosylceramides and Glucosylceramides as Electron Paramagnetic Probes 合成自旋标记的 α-/β-Galactosylceramides 和 Glucosylceramides 作为电子顺磁探针
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02423
Rajendra Rohokale, Rajendra Mane, Lucie Malet, Selena Dessain, Zhongwu Guo
{"title":"Synthesis of Spin-Labeled α-/β-Galactosylceramides and Glucosylceramides as Electron Paramagnetic Probes","authors":"Rajendra Rohokale, Rajendra Mane, Lucie Malet, Selena Dessain, Zhongwu Guo","doi":"10.1021/acs.joc.4c02423","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02423","url":null,"abstract":"α-/β-Galactosylceramide (GalCer) and glucosylceramide (GlcCer) derivatives having a radical label at the 6-<i>C</i>-position suitable for electron paramagnetic resonance spectroscopic studies were synthesized by a diversity-oriented strategy that is highlighted by the efficient glycosylation of a lipid precursor and late-stage ceramide assembly to enable lipid diversification. The strategy was also utilized to synthesize natural α-/β-GalCers and GlcCers. Furthermore, the involved azido-intermediates are flexible platforms to access various other GalCer and GlcCer derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"87 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832998","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Base-Promoted Sulfur Arylation of Sulfenamides to Oxonium Aryne Precursors: Chemoselective Synthesis of Sulfilimines and o-Sulfanylanilines
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02373
Wang-Liang Chen, Sheng Fang, Jia-Lin Song, Qiong Hu, Shang-Shi Zhang, Bing Shu
{"title":"Base-Promoted Sulfur Arylation of Sulfenamides to Oxonium Aryne Precursors: Chemoselective Synthesis of Sulfilimines and o-Sulfanylanilines","authors":"Wang-Liang Chen, Sheng Fang, Jia-Lin Song, Qiong Hu, Shang-Shi Zhang, Bing Shu","doi":"10.1021/acs.joc.4c02373","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02373","url":null,"abstract":"In this study, a metal-free and efficient method for the synthesis of sulfilimines and <i>o</i>-sulfanylanilines in high yields with excellent chemoselectivities from oxonium aryne precursors with sulfenamides has been developed. This method features mild reaction conditions, simple operations, a general substrate scope, and good tolerance of functional groups. In addition, scale-up synthesis, related applications, and preliminary mechanistic explorations were also investigated.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832806","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Bioinspired Synthesis of Phelligridin Analogues via Ru-Catalyzed C–H Activation/[4 + 2] Annulation of Aryl Imidates with Heteroaromatic Iodonium Ylides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02455
Mingdian Liang, Si-Jing Huang, Dongyang Zhang, Bei Wan, Shaoyu Mai, Huaming Tao
{"title":"Bioinspired Synthesis of Phelligridin Analogues via Ru-Catalyzed C–H Activation/[4 + 2] Annulation of Aryl Imidates with Heteroaromatic Iodonium Ylides","authors":"Mingdian Liang, Si-Jing Huang, Dongyang Zhang, Bei Wan, Shaoyu Mai, Huaming Tao","doi":"10.1021/acs.joc.4c02455","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02455","url":null,"abstract":"The first Ru(II)-catalyzed C–H activation/[4 + 2] annulation of aryl imidates with heteroaromatic iodonium ylides is reported. Our approach features the utilization of a commercially available ruthenium catalyst, providing a one-step construction of phelligridin analogues from easily available and nonpreactivated starting materials. The developed methodology is successfully employed for the total synthesis of phelligridin A, significantly streamlining previous multistep synthesis. The potential of this approach is further demonstrated through a modular synthesis of the core structure of phelligridin C/D.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"48 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832999","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Ring Opening of Diketene in Superacidic Media
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02601
Sebastian Steiner, Ulli Blumenschein, Zurwa M. Shafiq, Christoph Jessen, Alexander Nitzer, Christoph Taeschler, Andreas J. Kornath
{"title":"Ring Opening of Diketene in Superacidic Media","authors":"Sebastian Steiner, Ulli Blumenschein, Zurwa M. Shafiq, Christoph Jessen, Alexander Nitzer, Christoph Taeschler, Andreas J. Kornath","doi":"10.1021/acs.joc.4c02601","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02601","url":null,"abstract":"The reactions of diketene were investigated in the HF/MF<sub>5</sub> and DF/MF<sub>5</sub> (M = As or Sb) binary superacidic systems. Depending on the stoichiometric ratio of the Lewis acids and diketene, monoprotonated acetoacetyl fluoride and diprotonated acetoacetyl fluoride were obtained. The salts were characterized by low-temperature vibrational spectroscopy, nuclear magnetic resonance spectroscopy, and single-crystal X-ray diffraction. [CH<sub>3</sub>C(OH)CH<sub>2</sub>COF][SbF<sub>6</sub>]·HF crystallizes in monoclinic space group <i>P</i>2<sub>1</sub>/<i>n</i> with four formula units per unit cell, and [CH<sub>3</sub>C(OH)CH<sub>2</sub>C(OH)F][SbF<sub>6</sub>]<sub>2</sub>·HF in triclinic space group <i>P</i><span>1</span> with two formula units per unit cell. Ring opening is discussed together with quantum chemical p<i>K</i><sub>a</sub> calculations. Monoprotonated acetoacetyl fluoride is characterized by a six-membered ring-like structure containing an intramolecular hydrogen bond, whereas the diprotonated species constitutes a 1,3-gitonic superelectrophile.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"247 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833000","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Metal-Free Synthesis of 4-Bromoisoquinolines through Brominative Annulation of 2-Alkynyl Arylimidate Using In Situ-Generated Transient Bromoiodane
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02867
Akshay S. Pathare, Sermadurai Selvakumar
{"title":"Metal-Free Synthesis of 4-Bromoisoquinolines through Brominative Annulation of 2-Alkynyl Arylimidate Using In Situ-Generated Transient Bromoiodane","authors":"Akshay S. Pathare, Sermadurai Selvakumar","doi":"10.1021/acs.joc.4c02867","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02867","url":null,"abstract":"Herein, we report the <i>in situ</i>-generated transient bromoiodane-mediated brominative annulation of 2-alkynyl arylimidate for the synthesis of 4-bromoisoquinolines at room temperature. Using a simple hypervalent iodine reagent PIDA as a mild oxidant and potassium bromide as the halogen source, a broad range of valuable 4-bromoisoquinolines can be synthesized in excellent yields. The reaction features readily available chemicals, mild metal-free conditions, and high functional group tolerance, providing an efficient alternative for the construction of halogenated isoquinolines.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"77 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833001","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
TMSN3 Initiated Electrochemical Mono-Dealkylation of Tertiary Amides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1021/acs.joc.4c01813
Anjun Ding, Meixia Liu, Yunxiang Jiang, Xiaoyong Liu, Junpeng Yang, Wen Liu, Zhengjiang Fu, Shengmei Guo, Hu Cai
{"title":"TMSN3 Initiated Electrochemical Mono-Dealkylation of Tertiary Amides","authors":"Anjun Ding, Meixia Liu, Yunxiang Jiang, Xiaoyong Liu, Junpeng Yang, Wen Liu, Zhengjiang Fu, Shengmei Guo, Hu Cai","doi":"10.1021/acs.joc.4c01813","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01813","url":null,"abstract":"<i>N</i>-Dealkylation of amides is a general process in living organisms and organic synthetic chemistry, but an efficient chemical approach for this transformation has not been explored. Herein, we report an electrochemical method for the monodealkylation of a wide range of tertiary amides, including benzamides, alkyl amides, lactams, and sulfonamides. The reaction proceeds smoothly under mild conditions using TMSN<sub>3</sub> as the initiator and is not limited to deethylation or demethylation. This protocol enables the large synthesis, providing a valuable tool for synthetic organic chemistry.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816354","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Open-Flask Protocol for the Removal of Alloc Carbamate and Allyl Ester Protecting Groups. Application to In-solution and On-resin Peptide Synthesis
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1021/acs.joc.4c02115
Patrick Napier, Nicole Bakas, Abhijit Bhat, Alain Noncovich
{"title":"Open-Flask Protocol for the Removal of Alloc Carbamate and Allyl Ester Protecting Groups. Application to In-solution and On-resin Peptide Synthesis","authors":"Patrick Napier, Nicole Bakas, Abhijit Bhat, Alain Noncovich","doi":"10.1021/acs.joc.4c02115","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02115","url":null,"abstract":"The standard protocol for Alloc group removal during peptide synthesis still presents limitations, including low reaction yields, <i>N</i>-allylated byproducts, and the use of air-sensitive Pd(PPh<sub>3</sub>)<sub>4</sub>. We addressed these challenges by developing a novel protocol using the air-stable Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub> catalyst, Meldrum’s acid (MA), and triethylsilane (TES-H). This combination ensured high yields, eliminated <i>N</i>-allylated byproducts, and is compatible with automated synthesis. This cost-effective and efficient method shows promise for widespread use in peptide chemistry applications and beyond.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"42 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816355","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Two-Step Formation of Substituted Pyridines from Iodoenones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1021/acs.joc.4c02502
Carl Malenfant, Maxime Denis, Sylvain Canesi
{"title":"Two-Step Formation of Substituted Pyridines from Iodoenones","authors":"Carl Malenfant, Maxime Denis, Sylvain Canesi","doi":"10.1021/acs.joc.4c02502","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02502","url":null,"abstract":"A new access to substituted pyridines was developed from iodoenones. This two-step procedure involves a Sonogashira coupling with a free alkyne containing a nosylamide followed by a thiophenol treatment in basic conditions that triggers nosyl deprotection, a Michael–retro-Michael process, condensation, and isomerization in cascade to yield the heterocycle. This method enables the introduction of different substituents at several pyridine positions. This approach offers new synthetic opportunities to produce heterocycles present in many bioactive compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816358","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Azobis(polynitrophenyl-1,2,5-oxadiazoles) as Heat-Resistant Friction-Insensitive Energetic Materials
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1021/acs.joc.4c02678
Ilya D. Deltsov, Dmitry B. Vinogradov, Konstantin A. Monogarov, Leonid L. Fershtat
{"title":"Azobis(polynitrophenyl-1,2,5-oxadiazoles) as Heat-Resistant Friction-Insensitive Energetic Materials","authors":"Ilya D. Deltsov, Dmitry B. Vinogradov, Konstantin A. Monogarov, Leonid L. Fershtat","doi":"10.1021/acs.joc.4c02678","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02678","url":null,"abstract":"The evolution of energetic materials science presents new challenging tasks associated with the creation of advanced technologies for sustainable development of the future. In this work, a set of new heat-resistant high-energy materials incorporating the polynitrophenyl-1,2,5-oxadiazole scaffold enriched with azo/azoxy moieties have been designed and synthesized. Due to a smart combination of explosophoric groups and 1,2,5-oxadiazole rings, the prepared high-energy substances have excellent thermal stability (up to 300 °C), good densities (up to 1.75 g cm<sup>–3</sup>), high enthalpies of formation (340–538 kJ mol<sup>–1</sup>), and high combined nitrogen–oxygen content (63–68%). In-depth structural analysis revealed the presence of strong intra- and intermolecular hydrogen bonds in aminodinitrophenyl derivatives, which in combination with the small deviation of electrostatic potential values explains the low mechanical sensitivity of these materials. At the same time, trinitrophenyl-1,2,5-oxadiazoles incorporating three adjacent non-coplanar nitro groups demonstrated higher sensitivity to impact, albeit retaining complete insensitivity to friction. The overall performance of the thus prepared high-energy substances exceeds that of the known heat-resistant explosive hexanitrostilbene. Therefore, the newly synthesized family of energetic polynitrophenyl-1,2,5-oxadiazoles provides a fruitful foundation for the creation of the advanced heat-resistant energetic materials of the future.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"22 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816360","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 1,4,2-Diazaphospholidine-3,5-diones Using Na(OCP) as the “P” Source
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1021/acs.joc.4c02259
Yao Chai, Ya-Ling Tian, Wen-Bo Xu, Bo Yang, Zhi-Bin Wang, Dong-Ping Chen, Xi-Cun Wang, Zheng-Jun Quan
{"title":"Synthesis of 1,4,2-Diazaphospholidine-3,5-diones Using Na(OCP) as the “P” Source","authors":"Yao Chai, Ya-Ling Tian, Wen-Bo Xu, Bo Yang, Zhi-Bin Wang, Dong-Ping Chen, Xi-Cun Wang, Zheng-Jun Quan","doi":"10.1021/acs.joc.4c02259","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02259","url":null,"abstract":"A refined synthesis of 1,4,2-diazaphospholidine-3,5-dione derivatives was achieved through a cyclization reaction involving Na(OCP) and isocyanates. Na(OCP) was demonstrated to be a relatively stable and safe source of phosphorus, enabling the production of diverse 1,4,2-diazaphospholidine-3,5-dione derivatives with high yields. The reaction proceeds efficiently under catalyst-free and mild conditions. Both experimental findings and density functional theory calculations have elucidated that the process involves a crucial step of carbon monoxide elimination, which provides deeper insight into the reaction mechanism.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"226 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816356","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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