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Transition metal-free one-pot tandem chemoselective reduction and cyclization of 3/5-(2-nitrophenyl)-1H-pyrazoles using sodium dithionite. 二亚硝酸钠对3/5-（2-硝基苯）- 1h -吡唑的无过渡金属一锅串联化学选择性还原和环化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00610d
Danaboina Srikanth, Gayatri Diliprao Shejul, Swanand Vinayak Joshi, Abdul Kalam, Avvaru Subha Jahnavi, Amol G Dikundwar, Sidharth Chopra, Madhavi Venkata Yaddanapudi, Srinivas Nanduri
{"title":"Transition metal-free one-pot tandem chemoselective reduction and cyclization of 3/5-(2-nitrophenyl)-1<i>H</i>-pyrazoles using sodium dithionite.","authors":"Danaboina Srikanth, Gayatri Diliprao Shejul, Swanand Vinayak Joshi, Abdul Kalam, Avvaru Subha Jahnavi, Amol G Dikundwar, Sidharth Chopra, Madhavi Venkata Yaddanapudi, Srinivas Nanduri","doi":"10.1039/d5ob00610d","DOIUrl":"https://doi.org/10.1039/d5ob00610d","url":null,"abstract":"<p><p>A sodium dithionite (Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub>) mediated tandem chemoselective reductive cyclization of 5-(2-nitrophenyl)-1<i>H</i>-pyrazoles with aldehydes/carbon disulfide is developed for the synthesis of pyrazolo[1,5-<i>c</i>]quinazolines. The protocol involves one pot <i>in situ</i> reduction of 5-(2-nitrophenyl)-1<i>H</i>-pyrazoles, followed by intermolecular cyclization with aldehydes or carbon disulfide to afford the pyrazolo[1,5-<i>c</i>]quinazolines. The protocol is further expanded for the synthesis of pyrazolo[4,3-<i>c</i>]quinolines from 3-(2-nitrophenyl)-1-phenyl-1<i>H</i>-pyrazole-4-carbaldehyde <i>via</i> one pot <i>in situ</i> reduction followed by intramolecular cyclization. Notably, the use of Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub> as the reducing agent enables a metal, ligand, and additive-free approach, wide substrate scope, and scalability up to gram scale. The synthesized compounds were studied for photophysical properties in ACN and MeOH, the compound 7c, which contains an electron-donating methoxy group, exhibited a greater bathochromic shift. Notably, the pyrazolo[1,5-<i>c</i>]quinazoline-5(6<i>H</i>)-thione derivatives 5a and 5d demonstrated selective inhibition of <i>Staphylococcus aureus</i>, with minimum inhibitory concentrations (MICs) of 2 and 4 μg mL<sup>-1</sup>, respectively. ESI-MS and DFT studies were conducted for the identification of the key intermediates and to elucidate the plausible reaction mechanism.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144155230","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
n Bu4NBr-catalyzed esterification of methoxyarenes with acyl bromide. n bu4nbr催化甲氧基芳烃与酰基溴的酯化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00612k
Ting Sun, Wen Chao Zhu, Qin Zhu, Shao Yin Wang, Guo Dong Wang, Jiang-Fei Li
{"title":"<sup><i>n</i></sup> Bu<sub>4</sub>NBr-catalyzed esterification of methoxyarenes with acyl bromide.","authors":"Ting Sun, Wen Chao Zhu, Qin Zhu, Shao Yin Wang, Guo Dong Wang, Jiang-Fei Li","doi":"10.1039/d5ob00612k","DOIUrl":"https://doi.org/10.1039/d5ob00612k","url":null,"abstract":"<p><p>The catalytic esterification of methoxyarenes remains challenging, especially for C(sp<sup>3</sup>)-O bond functionalization. Herein, we report a simple and efficient method using <sup><i>n</i></sup>Bu<sub>4</sub>NBr as a catalyst to directly convert methoxyarenes and acyl bromides into esters under solvent-free conditions. This strategy provides a simple and efficient approach, achieving yields of up to 95%.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148717","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
Recent applications of Cyrene as a chiral synthon. 昔兰尼手性合成物的最新应用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00642b
Yu A Khalilova, L Kh Faizullina
{"title":"Recent applications of Cyrene as a chiral synthon.","authors":"Yu A Khalilova, L Kh Faizullina","doi":"10.1039/d5ob00642b","DOIUrl":"https://doi.org/10.1039/d5ob00642b","url":null,"abstract":"<p><p>Dihydrolevoglucosenone (Cyrene™) is a unique chiral molecule with great synthetic potential. Currently, Cyrene has been successfully used as a dipolar aprotonic solvent with green chemistry requirements, which is very important for both medicine and industry. There are several review articles on this topic, which we have referenced in this article. In this review, we describe the prospect of using Cyrene as a chiral molecule in organic synthesis, including an emphasis on the route to practically important objects based on it. The review presents chemical transformations of Cyrene by reactive centers (carbonyl and methylene groups, acetal center, anhydro bridge) with an eye to valuable chiral molecules and discusses the mechanism of some interesting transformations. We hope that the review will be useful to scientists working not only in organic but also in medicinal and polymer chemistry. The review summarizes the literature data for the last 10 years, with the rare exception of earlier works in view of the importance of using the published material.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126110","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
Catalytic dynamic kinetic reductive addition of simple aldehydes and aldimines with heterobiaryl triflates: harnessing both central and axial chirality. 简单醛和醛胺与三氟酸杂二芳酯的催化动力学还原加成：利用中心手性和轴向手性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00521c
Hui Ni, Anyao Liu, Xiaoying Fu, Xinyi Zhang, Xiaowen Xue, Xiang Lyu, Aijun Lin, Yuli He
{"title":"Catalytic dynamic kinetic reductive addition of simple aldehydes and aldimines with heterobiaryl triflates: harnessing both central and axial chirality.","authors":"Hui Ni, Anyao Liu, Xiaoying Fu, Xinyi Zhang, Xiaowen Xue, Xiang Lyu, Aijun Lin, Yuli He","doi":"10.1039/d5ob00521c","DOIUrl":"https://doi.org/10.1039/d5ob00521c","url":null,"abstract":"<p><p>A nickel-catalyzed intramolecular dynamic kinetic resolution (DKR) strategy has been developed for the enantioselective synthesis of axially chiral heterobiaryls from racemic azabiaryl triflates. Using a reductive addition mechanism, this method controls both axial and central chirality, offering broad substrate scope, excellent enantioselectivity, and atroposelectivity. The resulting chiral heterobiaryls were effectively employed as organocatalysts and chiral ligands in asymmetric transformations, highlighting their synthetic utility. Mechanistic studies indicate a synergy between kinetic resolution and nickel-mediated stereochemical inversion, addressing challenges in concurrent axial and stereochemical control.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126381","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
Rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes to access fused naphthalenes. 铑催化3-芳基异恶唑与1,6-二炔序贯双碳氢环化反应得到熔融萘。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00466g
Ramesh Kotipalli, T Mahipal Reddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
{"title":"Rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes to access fused naphthalenes.","authors":"Ramesh Kotipalli, T Mahipal Reddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy","doi":"10.1039/d5ob00466g","DOIUrl":"https://doi.org/10.1039/d5ob00466g","url":null,"abstract":"<p><p>Selective dual C-H annulations with 1,<i>n</i>-diunsaturated systems represent a powerful tool for constructing multicyclic scaffolds in an expeditious manner. Here, we report a rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes for napthofused polycyclic systems. Some kinetic isotopic experiments were carried out to understand the reaction mechanism and some downstream experiments were conducted to demonstrate the potential of the methodology. The method features a broad substrate scope and scale-up capability.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126113","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
Superacid-catalysed α-deuteration of ketones with D2O. 超强酸催化D2O对酮的α-氘化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00683j
Haiying Yuan, Kaibo Xu, Jinling Li, Teck-Peng Loh, Zhenguo Zhang, Zhenhua Jia
{"title":"Superacid-catalysed α-deuteration of ketones with D<sub>2</sub>O.","authors":"Haiying Yuan, Kaibo Xu, Jinling Li, Teck-Peng Loh, Zhenguo Zhang, Zhenhua Jia","doi":"10.1039/d5ob00683j","DOIUrl":"https://doi.org/10.1039/d5ob00683j","url":null,"abstract":"<p><p>In this study, we present a superacid catalyzed protocol for the α-deuteration of ketones with D<sub>2</sub>O using [Ph<sub>3</sub>C]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup> as a pre-catalyst to generate <i>in situ</i> the superacidic species [D]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup>. The features of this catalytic process include simple manipulation, high deuteration efficiency (up to 99%), excellent functional group compatibility and a broad substrate scope, including 30 substrates comprising common building blocks and bioactive molecules like pentoxifylline. Moreover, the avoidance of toxic reagents enables sustainable access to deuterated products, demonstrating the method's practical potential for use in mechanistic studies and pharmaceutical applications.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126115","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
Regioselective synthesis of α-(2-indolyl) ketones with arylaldehydes via a tandem reaction of 2-alkynylanilines. 2-炔基苯胺串联反应合成α-（2-吲哚基）酮与芳醛的区域选择性反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00288e
Jianwei Wang, Qingxia Zhao, Hangxiao Fu, Jie Li
{"title":"Regioselective synthesis of α-(2-indolyl) ketones with arylaldehydes <i>via</i> a tandem reaction of 2-alkynylanilines.","authors":"Jianwei Wang, Qingxia Zhao, Hangxiao Fu, Jie Li","doi":"10.1039/d5ob00288e","DOIUrl":"https://doi.org/10.1039/d5ob00288e","url":null,"abstract":"<p><p>A base-promoted synthesis of α-(2-indolyl) ketones (or 2-(α-aryl benzyl ketone) indoles) is developed <i>via</i> 5-<i>endo-dig</i> cyclization of 2-alkynylanilines, followed by aroylation of the resulting carbanion. This transition metal-free reaction proceeded with high regioselectivity and a wide substrate scope (46 examples, up to 93% yield). Among the syntheses of 2-substituted indoles, this tandem process is straightforward and convenient.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126111","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
Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF2COAr. 邻苯二胺- scf2coar有机催化β-酮酯的对映选择性α-二氟甲基酮硫代化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-22 DOI: 10.1039/d5ob00520e
Wenning Chang, En Wang, Junqing Liang, Xusheng Shao, Xiaoyong Xu, Wu-Lin Yang, Zhong Li
{"title":"Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF<sub>2</sub>COAr.","authors":"Wenning Chang, En Wang, Junqing Liang, Xusheng Shao, Xiaoyong Xu, Wu-Lin Yang, Zhong Li","doi":"10.1039/d5ob00520e","DOIUrl":"https://doi.org/10.1039/d5ob00520e","url":null,"abstract":"<p><p>The first asymmetric α-difluoromethylketone thiolation of diverse β-keto esters using an electrophilic phthalimide-SCF<sub>2</sub>COAr reagent (PhthN-SCF<sub>2</sub>COAr) was reported. In the presence of cinchona-alkaloid-based catalyst (DHQD)<sub>2</sub>PHAL, the reaction was achieved in moderate yields with a moderate to excellent enantioselectivity (up to 93% ee) under mild reaction conditions and exhibited functional group compatibility. An ammonium hydrogen-bonded induction model was proposed to rationalize the origin of enantioselectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144118380","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
Systematic investigation of the structure-property relationship of substituted p-alkoxy-azothiophenes. 取代对烷氧基偶氮噻吩构效关系的系统研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-22 DOI: 10.1039/d5ob00506j
Conrad Averdunk, Hermann A Wegner
{"title":"Systematic investigation of the structure-property relationship of substituted <i>p</i>-alkoxy-azothiophenes.","authors":"Conrad Averdunk, Hermann A Wegner","doi":"10.1039/d5ob00506j","DOIUrl":"https://doi.org/10.1039/d5ob00506j","url":null,"abstract":"<p><p>Differently substituted <i>p</i>-alkoxy azothiophenes with increasing alkoxy chains were systematically investigated in terms of their structure-property relationships. In particular, it was observed that increasing the length of the alkoxy chain had an unusual effect on the melting point, which did not follow the expected odd-even effect. It was also shown that changing the length of the alkoxy chain did not significantly affect the thermal half-life, a finding that disagrees with results reported in other studies. These observations provide valuable insights into structure-property relationships with important implications for the design and development of azobenzenes as molecular materials for various applications. Furthermore, each <i>p</i>-alkoxy azothiophene was investigated in terms of neat solid-state photoisomerisation or photoinduced liquefaction, which is a critical parameter for application as a molecular solar thermal phase-change (MOST-PCM) energy storage system.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144118382","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-triggered organophotoredox-catalyzed oxidation of 3-(benzylidine)indoline to indole-3-carbinols and 3-acyl indoles. 可见光触发的有机光氧化还原催化3-（苄基）吲哚氧化为吲哚-3-甲醇和3-酰基吲哚。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-21 DOI: 10.1039/d5ob00401b
Sourav Ghosh, Gopal Rana, Abhishek Kar, Rajkamal Sahoo, Umasish Jana
{"title":"Visible-light-triggered organophotoredox-catalyzed oxidation of 3-(benzylidine)indoline to indole-3-carbinols and 3-acyl indoles.","authors":"Sourav Ghosh, Gopal Rana, Abhishek Kar, Rajkamal Sahoo, Umasish Jana","doi":"10.1039/d5ob00401b","DOIUrl":"https://doi.org/10.1039/d5ob00401b","url":null,"abstract":"<p><p>A visible-light-triggered, Eosin-Y-catalyzed oxidative isomerization/carbon-oxygen bond formation of 3-(benzylidine) indolines has been explored to afford structurally diverse indole-3-carbinols and 3-acyl indoles in good-to-excellent yields. This new protocol is metal-free and features mild reaction conditions, easily available starting materials, and environmentally benign reaction conditions. A preliminary mechanistic study reveals that initially, an iminium ion-radical intermediate is formed <i>via</i> a single electron transfer (SET) mechanism, which facilitates cascade isomerization and C-O bond formation through the nucleophilic addition of H<sub>2</sub>O.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144109180","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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