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Effective self-assembly of 21- and 14-membered azamacrocycles via condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors. 通过不同硫代氨基氮基前驱体的条件控制环三聚化或环二聚化，有效自组装 21 元和 14 元氮杂环。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4ob01384k
Anastasia A Fesenko, Mikhail S Grigoriev, Anatoly D Shutalev
{"title":"Effective self-assembly of 21- and 14-membered azamacrocycles <i>via</i> condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors.","authors":"Anastasia A Fesenko, Mikhail S Grigoriev, Anatoly D Shutalev","doi":"10.1039/d4ob01384k","DOIUrl":"https://doi.org/10.1039/d4ob01384k","url":null,"abstract":"<p><p>A preparative synthesis of previously unknown 21- and 14-membered azamacrocycles <i>via</i> acid-promoted cyclotrimerization or cyclodimerization of three readily available precursors, namely, 1-amino-6-hydroxy-4,6-dimethylhexahydropyrimidine-2-thione, 4-(4-oxopent-2-yl)thiosemicarbazide hydrazone, and 5,7-dimethyl-1,4,5,6-tetrahydro-3<i>H</i>-1,2,4-triazepine-3-thione has been developed. A dramatic dependence of the selectivity of macrocyclization on the reaction conditions is demonstrated. The thermodynamic aspects of the reactions are discussed based on experimental data and DFT calculation results. Plausible pathways for the formation of macrocycles are proposed.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453678","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Reversible encapsulation and release of fullerenes using calix[n]phenoxazines. 使用钙[n]吩噁嗪对富勒烯进行可逆封装和释放。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4ob01569j
Lu Wang, Yunxiao Li, Xin Qu, Da Ma, M Zubair Iqbal, Xiangdong Kong, Lijun Mao
{"title":"Reversible encapsulation and release of fullerenes using calix[<i>n</i>]phenoxazines.","authors":"Lu Wang, Yunxiao Li, Xin Qu, Da Ma, M Zubair Iqbal, Xiangdong Kong, Lijun Mao","doi":"10.1039/d4ob01569j","DOIUrl":"10.1039/d4ob01569j","url":null,"abstract":"<p><p>This investigation presents the synthesis of butyl-decorated calix[<i>n</i>]phenoxazines of varying sizes by kinetic control and the ring-expansion of calix[3]phenoxazine, which uniquely exhibits distinct binding affinities for fullerenes C<sub>60</sub> and C<sub>70</sub>. Calix[3]phenoxazine demonstrates a higher binding affinity for cationic ammonium, which can be reversibly deprotonated and protonated, enabling the reversible release and reloading of fullerenes. This system holds potential for applications in fullerene extraction and separation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453694","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid. 手性磷酸促成肉桂醛衍生的 N-芳基硝基与 2-吲哚甲醇的不对称 [3 + 3] 环加成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4ob01365d
Ning Zou, Yu-Zheng Wu, Zi-Wei Shang, Yu-Wei Cao, Li-Min Liao, Cui Wei, Dong-Liang Mo, Wen-Jun Zhou
{"title":"Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived <i>N</i>-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid.","authors":"Ning Zou, Yu-Zheng Wu, Zi-Wei Shang, Yu-Wei Cao, Li-Min Liao, Cui Wei, Dong-Liang Mo, Wen-Jun Zhou","doi":"10.1039/d4ob01365d","DOIUrl":"https://doi.org/10.1039/d4ob01365d","url":null,"abstract":"<p><p>We described a chiral phosphoric acid (CPA) catalyzed asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived <i>N</i>-aryl nitrones with 2-indolylmethanols to prepare various indole-fused 1,2-oxazines in high yields (up to 96%) with excellent enantioselectivity (>99% ee). Control experiments indicate that hydrogen bonding plays important roles in controlling the enantioselectivity of products. This strategy provides an efficient pathway to construct enantioenriched indole-fused 1,2-oxazines from <i>N</i>-aryl nitrones with 2-indolylmethanols.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453671","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Benzylamine promoted direct C-H arylation of arenes and heteroarenes via excitation with heat or light. 通过热或光的激发，苄胺促进了炔类化合物和杂环戊烯的直接 C-H 芳基化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-21 DOI: 10.1039/d4ob01377h
Souvik Chatterjee, Sabnam Azmi, Nilaj Bandopadhyay, Krishnendu Paramanik, Gayetri Sarkar, Bhaskar Biswas, Hari Sankar Das
{"title":"Benzylamine promoted direct C-H arylation of arenes and heteroarenes <i>via</i> excitation with heat or light.","authors":"Souvik Chatterjee, Sabnam Azmi, Nilaj Bandopadhyay, Krishnendu Paramanik, Gayetri Sarkar, Bhaskar Biswas, Hari Sankar Das","doi":"10.1039/d4ob01377h","DOIUrl":"https://doi.org/10.1039/d4ob01377h","url":null,"abstract":"<p><p>Carbon-halogen bond cleavage in aryl halides through single electron transfer (SET) is a crucial step in radical-based cross-coupling reactions. Accomplishing such cleavage using an organic system without the assistance of any transition metal-based catalyst is highly challenging. In recent years, combining organic molecules and a base has served as a unique system for SET-mediated carbon-halogen bond cleavage. Herein, we report the combination of simple benzylamine and potassium <i>tert</i>-butoxide as a super-electron-donor system for SET-mediated cleavage of aryl halides generating reactive aryl radicals, which subsequently react with arenes or heteroarenes and produce biaryl skeletons. The new methodology enables the arylation of arenes and heteroarenes with aryl iodides, or aryl bromides, upon excitation with heat or light. The broad substrate scope, mild reaction conditions and tolerance of common organic functional groups offer an efficient alternative route for direct C-H arylation reactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453673","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
BF3·OEt2-catalyzed/mediated alkyne cyclization: a comprehensive review of heterocycle synthesis with mechanistic insights. BF3-OEt2 催化/介导的炔环化：杂环合成的全面回顾与机理启示。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-21 DOI: 10.1039/d4ob01426j
Priya Ghosh, Anil K Saikia
{"title":"BF<sub>3</sub>·OEt<sub>2</sub>-catalyzed/mediated alkyne cyclization: a comprehensive review of heterocycle synthesis with mechanistic insights.","authors":"Priya Ghosh, Anil K Saikia","doi":"10.1039/d4ob01426j","DOIUrl":"https://doi.org/10.1039/d4ob01426j","url":null,"abstract":"<p><p>The quest for efficient and versatile methods for heterocycle synthesis continues to drive innovation in organic chemistry. In this context, the cyclization of alkynes catalyzed or mediated by boron trifluoride diethyl etherate (BF<sub>3</sub>·OEt<sub>2</sub>) has emerged as a powerful and widely applicable strategy. This review provides a comprehensive and authoritative overview of BF<sub>3</sub>·OEt<sub>2</sub>-catalyzed/mediated alkyne cyclization reactions, covering the scope, mechanisms, and applications of these processes. We discuss the synthesis of a diverse range of heterocyclic compounds, including dihydropyrans, quinolines, dehydropiperidines, oxindoles and others, and highlight the unique advantages of BF<sub>3</sub>·OEt<sub>2</sub> as a catalyst/mediator. Recent advances, challenges, and future directions in this rapidly evolving field are also addressed. This review aims to serve as a valuable resource for synthetic chemists, inspiring further research and applications in this exciting area.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
The synthesis of aryl amines enabled by rearrangement and demethylaromatization of cyclohexadienimines. 通过环己二烯亚胺的重排和脱甲基芳香化合成芳基胺。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-21 DOI: 10.1039/d4ob01338g
Xueyu Fang, Hongyan Xie, Hongkun Huang, Yu Wang, Tian Chen, Zhaohua Yan, Hua Yao
{"title":"The synthesis of aryl amines enabled by rearrangement and demethylaromatization of cyclohexadienimines.","authors":"Xueyu Fang, Hongyan Xie, Hongkun Huang, Yu Wang, Tian Chen, Zhaohua Yan, Hua Yao","doi":"10.1039/d4ob01338g","DOIUrl":"https://doi.org/10.1039/d4ob01338g","url":null,"abstract":"<p><p>The rearrangement and demethylaromatization of cyclohexadienimines (namely cyclohexadienone imines) were investigated in detail under metal-free conditions. Treating 4-aryl-4-methylcyclohexadienimines with acyl chloride at 100 °C in dichloromethane led to the smooth formation of <i>m</i>-arylaniline derivatives in good to excellent yields, in which [1,2]-migration of the aryl group at C-4 occurred exclusively. The demethylaromatization of 4-aryl-4-methylcyclohexadienimines mediated by iodotriphenylphosphonium iodide (<i>in situ</i> prepared <i>via</i> the reaction of triphenylphosphine with iodine) in toluene at 100 °C proceeded well, generating <i>p</i>-arylanilines in moderate to good yields. An efficient and alternative method for the synthesis of polysubstituted aryl amines, especially <i>m</i>-arylaniline derivatives which are otherwise difficult to synthesize through traditional methods, was developed.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453704","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
β-meso-Fused pyrene-porphyrin scaffolds with panchromatic absorption features. 具有全色吸收特征的β-介质融合芘卟啉支架。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-18 DOI: 10.1039/d4ob01447b
Christoph Oleszak, Christian L Ritterhoff, Bernd Meyer, Norbert Jux
{"title":"β-<i>meso</i>-Fused pyrene-porphyrin scaffolds with panchromatic absorption features.","authors":"Christoph Oleszak, Christian L Ritterhoff, Bernd Meyer, Norbert Jux","doi":"10.1039/d4ob01447b","DOIUrl":"https://doi.org/10.1039/d4ob01447b","url":null,"abstract":"<p><p>The π-extension of porphyrins with pyrenes through the β-<i>meso</i>-fusion of five-membered rings is demonstrated. Three architectures resulting from combining up to two porphyrins and pyrenes were obtained straightforwardly in good overall yields. Although significantly planarized, the molecules retain excellent solubility and processability. Spectroscopic characterization and density-functional theory calculations reveal intriguing absorption features.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Total synthesis, stereochemical assignment, and biological evaluation of opantimycin A and analogues thereof. 欧潘霉素 A 及其类似物的全合成、立体化学分配和生物学评价。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-18 DOI: 10.1039/d4ob01475h
Yoshinosuke Usuki, Ryota Abe, Kazuki Nishiguchi, Tetsuya Satoh, Harumi Aono, Toshihiko Nogawa, Yushi Futamura, Hiroyuki Osada, Izumi Yoshida, Kazuhiro Fujita, Takashi Mishima, Ken-Ichi Fujita
{"title":"Total synthesis, stereochemical assignment, and biological evaluation of opantimycin A and analogues thereof.","authors":"Yoshinosuke Usuki, Ryota Abe, Kazuki Nishiguchi, Tetsuya Satoh, Harumi Aono, Toshihiko Nogawa, Yushi Futamura, Hiroyuki Osada, Izumi Yoshida, Kazuhiro Fujita, Takashi Mishima, Ken-Ichi Fujita","doi":"10.1039/d4ob01475h","DOIUrl":"https://doi.org/10.1039/d4ob01475h","url":null,"abstract":"<p><p>Opantimycin A, a rare antimycin-class antibiotic without the macrolide core, was isolated from <i>Streptomyces</i> sp. RK88-1355 in 2017. In this study, we explored the total synthesis and stereochemical assignment of opantimycin A. The synthesis of all potential diastereomers has been accomplished <i>via</i> traceless Staudinger ligation. A comparison of the spectroscopic data of the synthesized compounds with that reported for the natural product confirmed that the absolute configuration of the natural product was (14<i>S</i>,17<i>R</i>,21<i>R</i>). Two analogous compounds were prepared, where the Dhb ((<i>Z</i>)-dehydrobutyrine) moiety was replaced with Dha (dehydroalanine) or ΔVal moieties, respectively. The inhibitory activities of these synthetic compounds against the production of the anti-inflammatory cytokine IL-6 were evaluated, and two potential candidates for further development as anti-inflammatory agents were identified.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453705","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
DMTSF-mediated electrophilic cyclization for the synthesis of 3-thiomethyl-substituted benzo[b]furan derivatives. DMTSF 介导的亲电环化合成 3-硫代甲基苯并[b]呋喃衍生物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-18 DOI: 10.1039/d4ob00958d
Declan T McGurk, Langley E Knighten, Maria J Peña Bú, Faith I Christofferson, Sierra D Rich, Prerna J Masih, Tanay Kesharwani
{"title":"DMTSF-mediated electrophilic cyclization for the synthesis of 3-thiomethyl-substituted benzo[<i>b</i>]furan derivatives.","authors":"Declan T McGurk, Langley E Knighten, Maria J Peña Bú, Faith I Christofferson, Sierra D Rich, Prerna J Masih, Tanay Kesharwani","doi":"10.1039/d4ob00958d","DOIUrl":"https://doi.org/10.1039/d4ob00958d","url":null,"abstract":"<p><p>Benzofuran is an important backbone for molecules that make up several pharmaceuticals, herbicides/pesticides, and organo-electronics. An environmentally benign dimethyl(methylthio)sulfonium tetrafluoroborate salt was used as an electrophile to induce cyclization of <i>o</i>-alkynyl anisoles to form 2,3-disubstituted benzofurans. The cyclization is performed at ambient reaction conditions, only takes 12 hours to get excellent yields, and shows a high tolerance for various substituted alkynes. Also, a sulfurmethyl group obtained after the cyclization reactions allows for a cascade cyclization, and an alkyne is used in the reaction to create a thieno[3,2-<i>b</i>]benzofuran core structure.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453677","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Visible-light-driven catalyst-free C-S cross-coupling of thiol derivatives and aryl halides. 硫醇衍生物与芳基卤化物的可见光驱动无催化剂 C-S 交叉偶联。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-18 DOI: 10.1039/d4ob01415d
Zhiqiang Liu, Yansong Hu, Shutao Wang, Yating Ding, Zhengze Zhang, Yi-Feng Qiu, Zhao Liu, Junqiang Lei
{"title":"Visible-light-driven catalyst-free C-S cross-coupling of thiol derivatives and aryl halides.","authors":"Zhiqiang Liu, Yansong Hu, Shutao Wang, Yating Ding, Zhengze Zhang, Yi-Feng Qiu, Zhao Liu, Junqiang Lei","doi":"10.1039/d4ob01415d","DOIUrl":"https://doi.org/10.1039/d4ob01415d","url":null,"abstract":"<p><p>A mild, scalable, and high-yielding visible-light-promoted C-S cross-coupling between alkyl thiol derivatives and (hetero)aryl halides without the need for metals, ligands, or photocatalysts is reported, offering advantages over traditional C-S bond forming strategies. The formation of an electron donor-acceptor (EDA) complex is supported by experimental and computational mechanistic studies, which undergoes visible-light-induced charge transfer to initiate C-S bond formation in the absence of a photoredox catalyst.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453707","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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