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Recent advances in the multicomponent synthesis of pyrazoles. 吡唑多组分合成的最新进展。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01211a
Jing Zhou, Quanquan Zhou, Jie-Ping Wan
{"title":"Recent advances in the multicomponent synthesis of pyrazoles.","authors":"Jing Zhou, Quanquan Zhou, Jie-Ping Wan","doi":"10.1039/d4ob01211a","DOIUrl":"https://doi.org/10.1039/d4ob01211a","url":null,"abstract":"<p><p>Pyrazole moiety is considered as an important N-heterocycle in pharmaceuticals and many other functional molecules. The utilization of multicomponent reaction is a major tool in the current approaches of pyrazole synthesis. Considering the power and significance of multicomponent pyrazole synthesis, we review herein the latest developments in this field. According to the typical features, the contents are divided into reactions with different NN fragment sources, such as hydrazine, hydrazone, amidine, nitrile, and diazo compounds, in the pyrazole ring construction, covering the works published since 2019 to date.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277425","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
Fe(III)-catalyzed p-selective C-H bond chalcogenation of phenols. Fe(III)-catalyzed p-selective C-H bond chalcogenation of phenols.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01382d
Biprajit Paul, Sayak Ghosh, Surajit Das, Indranil Chatterjee
{"title":"Fe(III)-catalyzed <i>p</i>-selective C-H bond chalcogenation of phenols.","authors":"Biprajit Paul, Sayak Ghosh, Surajit Das, Indranil Chatterjee","doi":"10.1039/d4ob01382d","DOIUrl":"https://doi.org/10.1039/d4ob01382d","url":null,"abstract":"<p><p>An efficient, eco-friendly, and scalable protocol has been introduced for the <i>p</i>-selective C-X (X = Se/S) bond formation of phenols employing earth-abundant, less-toxic Fe(III)-catalysts and the green solvent ethanol without using any directing template, stabilizing ligands, oxidants, or additives. The key attraction lies in the impressive <i>p</i>-selectivity with moderate to good yields, wide functional group compatibility under mild aerobic reaction conditions, and the synthetic modification of the products towards value-added molecules.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277422","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
Amide-derived enols in enol-Ugi reactions: expanding horizons for peptidomimetic scaffold synthesis. 烯醇-乌基反应中的酰胺衍生烯醇：拓宽拟肽支架合成的视野。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01216j
José Luis Ramiro, Ana G Neo, Carlos F Marcos
{"title":"Amide-derived enols in enol-Ugi reactions: expanding horizons for peptidomimetic scaffold synthesis.","authors":"José Luis Ramiro, Ana G Neo, Carlos F Marcos","doi":"10.1039/d4ob01216j","DOIUrl":"https://doi.org/10.1039/d4ob01216j","url":null,"abstract":"<p><p>A highly efficient enol-Ugi reaction of β,β-diketoamides has been developed using a novel non-heterocyclic amide-stabilised enol. This approach enables a broad reaction scope, affording β-enaminoamide peptidomimetics with constrained conformations due to CH-π interaction and C(sp<sup>3</sup>)H⋯O hydrogen bonding. Notably, the use of a five-membered cyclic enol is crucial for achieving stable products in excellent yields. This work highlights the potential of the enol-Ugi reaction for constructing diverse peptidomimetic scaffolds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277417","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
Palladium-catalyzed hydroarylation of 1,3-diynes with arylboronic acids. 钯催化的 1,3- 二炔与芳基硼酸的加氢反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01394h
Hongtao Shen, Xiaoyu Chen, Jianhua Qiu, Mengqi Chen, Bohai Zhang, Zhiyong Wu
{"title":"Palladium-catalyzed hydroarylation of 1,3-diynes with arylboronic acids.","authors":"Hongtao Shen, Xiaoyu Chen, Jianhua Qiu, Mengqi Chen, Bohai Zhang, Zhiyong Wu","doi":"10.1039/d4ob01394h","DOIUrl":"https://doi.org/10.1039/d4ob01394h","url":null,"abstract":"<p><p>Transition-metal-catalyzed selective hydroarylation of alkynes represents a state-of-the-art approach in organic chemistry. Herein, we report the reaction of symmetrical 1,3-diynes and arylboronic acids, with Pd(OAc)<sub>2</sub> as the catalyst and PCy<sub>3</sub> as the ligand, affording functionalized enynes in good to excellent yields. Its efficiency is demonstrated by its good functional group tolerance and broad substrate scope. This method offers a general, convenient, and practical strategy for the modular synthesis of multisubstituted enynes. To comprehensively elucidate the mechanism of the Pd-based catalytic system in the hydroarylation of 1,3-diynes, we performed detailed DFT computations for the Pd-catalyzed hydroarylation reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277424","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
Iridium-catalyzed reduction of o-hydroxyl phenyl enaminones for the synthesis of propiophenones and their application in 3-methyl chromone synthesis. 铱催化邻羟基苯基烯酮还原合成苯丙酮及其在 3-甲基铬酮合成中的应用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01359j
Zhi Tu, Jie-Ping Wan, Li Wei, Yunyun Liu
{"title":"Iridium-catalyzed reduction of <i>o</i>-hydroxyl phenyl enaminones for the synthesis of propiophenones and their application in 3-methyl chromone synthesis.","authors":"Zhi Tu, Jie-Ping Wan, Li Wei, Yunyun Liu","doi":"10.1039/d4ob01359j","DOIUrl":"https://doi.org/10.1039/d4ob01359j","url":null,"abstract":"<p><p>A method of reducing <i>o</i>-hydroxyphenyl enaminones with silane as the reductant to provide <i>o</i>-hydroxyl propiophenones has been achieved with iridium catalysis. The reduction reactions were found to proceed <i>via</i> the assistance of the hydroxyl group in the phenyl ring. In addition, the <i>o</i>-hydroxyl propiophenone products were used for the easy synthesis of 3-methyl chromones by directly incorporating <i>N</i>,<i>N</i>-dimethyl formamide dimethyl acetal (DMF-DMA) without using any catalyst.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277423","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
Deciphering the Knoevenagel condensation: towards a catalyst-free and water-mediated process. 解密克诺文纳格尔缩合：实现无催化剂和水介导的过程。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01420k
Periklis X Kolagkis, Stamatis K Serviou, Naya A Stini, Vera P Demertzidou, Efthymios T Poursaitidis, Eirini M Galathri, Olga G Mountanea, Elpida Skolia, Christoforos G Kokotos
{"title":"Deciphering the Knoevenagel condensation: towards a catalyst-free and water-mediated process.","authors":"Periklis X Kolagkis, Stamatis K Serviou, Naya A Stini, Vera P Demertzidou, Efthymios T Poursaitidis, Eirini M Galathri, Olga G Mountanea, Elpida Skolia, Christoforos G Kokotos","doi":"10.1039/d4ob01420k","DOIUrl":"https://doi.org/10.1039/d4ob01420k","url":null,"abstract":"<p><p>The Knoevenagel condensation constitutes one of the most well-studied and crucial transformations in organic chemistry, since it facilitates the synthesis of numerous valuable compounds. With the advent of green chemistry, several alternative protocols for the Knoevenagel reaction have been introduced and catalyst-free approaches to the Knoevenagel condensation have also been mentioned, however the harsh temperatures employed and the limited substrate scope restricted their application. Herein, we have performed an extensive study on the catalyst-free and water-mediated Knoevenagel reaction, with specific focus on optimising the green parameters and metrics of our methodology. Additionally, we directly compared our approach with previous catalyst-free methods, while providing a fast assembly of multiple compounds in parallel.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277420","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
A rapid approach towards a specific carbazolelactam system related to calothrixin B. 研究与卡洛曲星 B 有关的特异性咔唑内酰胺系统的快速方法。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01351d
Zizhen Wang, Sheng Liu
{"title":"A rapid approach towards a specific carbazolelactam system related to calothrixin B.","authors":"Zizhen Wang, Sheng Liu","doi":"10.1039/d4ob01351d","DOIUrl":"https://doi.org/10.1039/d4ob01351d","url":null,"abstract":"<p><p>Reported here is a rapid and versatile synthetic approach towards the specific pentacyclic carbazolelactams related to calothrixin B. The crucial transformation is an acid-promoted cascade involving a dehydration/electrocyclization/C-N bond cleavage/lactamization sequence.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277415","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
α-(N-Alkyl-N-heteroarenium)-α-diazoacetates: synthesis and reactivity of a novel class of ‘onium’ diazo compounds α-(N-烷基-N-庚烯)-α-重氮乙酸酯：一类新型 "鎓 "重氮化合物的合成和反应活性
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-18 DOI: 10.1039/d4ob01056f
Ya-Xi Li, Quan-Yun Liu, Yi Zhang, Miao-Miao Liu, Xiaoqian Liu, Mei-Hua Shen, Fang-Ming Wang, Hua-Dong Xu
{"title":"α-(N-Alkyl-N-heteroarenium)-α-diazoacetates: synthesis and reactivity of a novel class of ‘onium’ diazo compounds","authors":"Ya-Xi Li, Quan-Yun Liu, Yi Zhang, Miao-Miao Liu, Xiaoqian Liu, Mei-Hua Shen, Fang-Ming Wang, Hua-Dong Xu","doi":"10.1039/d4ob01056f","DOIUrl":"https://doi.org/10.1039/d4ob01056f","url":null,"abstract":"Treatment of alkyl α-(<em>N</em>-heteroaryl)-α-diazoacetates with alkylating reagents affords diazoacetate N-heteroarenium salts. These novel ‘onium’ diazo compounds are mostly yellow solids, displaying increased thermal and acid stability. Their tetrafluoroborates undergo rhodium catalyzed [2 + 1] and Doyle–Kirmse reactions under mild conditions, suggesting the <em>N</em>-quaternization an effective means of elimination of <em>N</em>-coordination caused catalyst toxicity.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142249933","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
Pyrrolizinofluorene-embedded dithiacalixcorrole(1.0.1.1)s 蕴含吡咯烷芴的二硫杂六环（1.0.1.1）s
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-18 DOI: 10.1039/d4ob01276c
Pooja Varak, Mangalampalli Ravikanth
{"title":"Pyrrolizinofluorene-embedded dithiacalixcorrole(1.0.1.1)s","authors":"Pooja Varak, Mangalampalli Ravikanth","doi":"10.1039/d4ob01276c","DOIUrl":"https://doi.org/10.1039/d4ob01276c","url":null,"abstract":"An unprecedented synthesis of pyrrolizinofluorene moiety embedded dithiacalixcorrole(1.0.<em>1</em>.<em>1</em>)s <em>via</em> [3 + 2] condensation of fluorene-based tripyrrane and appropriate bithiophene diol under TFA-catalyzed conditions is reported. Single crystal X-ray structural analysis revealed that the fluorene unit was inverted and involved in the intramolecular C–N bond formation, resulting in the generation of an unusual pyrrolizinofluorene moiety as part of the dithiacalixcorrole(1.0.<em>1</em>.<em>1</em>) framework. These macrocycles exhibit strong absorption in the UV-visible region and electrochemical studies revealed their electron-rich nature.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142249931","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
A comprehensive understanding of the mechanism of the biomimetic total synthesis of brevianamide A. 全面了解生物仿生全合成布雷维纳酰胺 A 的机理。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-18 DOI: 10.1039/d4ob00915k
Wenqiang Xu, Tian-Yu Sun, Yingtong Di, Xiaojiang Hao, Yun-Dong Wu
{"title":"A comprehensive understanding of the mechanism of the biomimetic total synthesis of brevianamide A.","authors":"Wenqiang Xu, Tian-Yu Sun, Yingtong Di, Xiaojiang Hao, Yun-Dong Wu","doi":"10.1039/d4ob00915k","DOIUrl":"https://doi.org/10.1039/d4ob00915k","url":null,"abstract":"<p><p>Recently, several studies on the chemical synthesis of brevianamide A (BA) were reported. In particular, a highly efficient and remarkably selective synthetic strategy was reported by Lawrence's group. However, a unified mechanistic understanding of these results is still lacking. We have carried out a DFT study and proposed a unified mechanism to understand these experimental results. Starting from intermediate 2, the most favorable reaction sequence is a fast tautomerization, followed by a σ-migration of the base moiety, and a final inverse-electron demanding Diels-Alder reaction, resulting in the formation of the BA product stereoselectively. This reaction mechanism can also be applied to understand the biosynthesis of BA that involves enzymatic catalysis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277414","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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