发布求助
文献互助 智能选刊 最新文献

Organic & Biomolecular Chemistry最新文献

筛选
英文 中文
Investigation of the photochemical behavior of allomaltol-containing 2-aminothiazole derivatives.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00264h
Alexander V Migulin, Constantine V Milyutin, Boris V Lichitsky, Stepan M Korobkov, Andrey N Komogortsev
{"title":"Investigation of the photochemical behavior of allomaltol-containing 2-aminothiazole derivatives.","authors":"Alexander V Migulin, Constantine V Milyutin, Boris V Lichitsky, Stepan M Korobkov, Andrey N Komogortsev","doi":"10.1039/d5ob00264h","DOIUrl":"https://doi.org/10.1039/d5ob00264h","url":null,"abstract":"<p><p>In the present communication, a comprehensive study of the photochemical behavior of terarylenes with a 2-aminothiazole bridge unit and an allomaltol substituent was performed. It was shown that for the considered substrates, two types of photoprocesses can be realized. By controlling the structure of the starting material, the photoprocess can be directed toward the 6π-electrocyclization of the 1,3,5-hexatriene system or the ESIPT-induced contraction of the pyranone ring. Relying on data from DFT calculations and UV-vis spectroscopy, the key features of the observed phototransformations were discussed. The investigated thiazole-containing terarylenes were utilized as a scaffold for the construction of photoacid generators (PAGs). Based on the performed research, a synthetic methodology was developed leading to series of 23 novel polycyclic photoproducts and a set of thiazole-containing salts with a quinoxaline part.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143762767","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
One-pot chemoselective aerobic synthesis of allyl-aryl sulfinyls by photoinduced Na2 - eosin Y.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5ob00181a
Trinadh Ballanki, Aishwarya Subramanian, Baby Viswambharan
{"title":"One-pot chemoselective aerobic synthesis of allyl-aryl sulfinyls by photoinduced Na<sub>2</sub> - eosin Y.","authors":"Trinadh Ballanki, Aishwarya Subramanian, Baby Viswambharan","doi":"10.1039/d5ob00181a","DOIUrl":"https://doi.org/10.1039/d5ob00181a","url":null,"abstract":"<p><p>Allyl-aryl sulfinyls are ubiquitous in medicine as well as in catalysis. Chemoselective synthesis of allyl-aryl sulfinyls is challenging due to competitive isomerization and overoxidation of allylic C-H bonds as well as sulfur. Herein, we have accomplished an unprecedented, metal-free, one-pot protocol for the aerobic synthesis of allyl-aryl sulfinyls from Morita-Baylis-Hillman allyl bromides and thiols under visible light photocatalysis through a radical pathway. Interestingly, this selective and controlled oxidation of <i>in situ</i>-formed allyl-aryl sulfides by the sub-stoichiometric oxidizing agent TEMPO <i>via</i> visible-light photocatalysis is well tolerated by an array of allyl bromides and thiols. This approach provides an efficient one-step route to the anti-cancer molecule INF<sub>50</sub>, and its synthetic application is demonstrated by an interrupted Pummerer reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143762465","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
Correction: Metal-free amination of alkenes based on maleimides
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-02 DOI: 10.1039/D5OB90043C
Li-Wen Shen, Shuang-Ling Lei, Hong-Yan Wang, Xin Wang, Lin-Mu Lu, Guang-Wei Wang, Yun-Qing Jia and Min Xiang
{"title":"Correction: Metal-free amination of alkenes based on maleimides","authors":"Li-Wen Shen, Shuang-Ling Lei, Hong-Yan Wang, Xin Wang, Lin-Mu Lu, Guang-Wei Wang, Yun-Qing Jia and Min Xiang","doi":"10.1039/D5OB90043C","DOIUrl":"10.1039/D5OB90043C","url":null,"abstract":"<p >Correction for ‘Metal-free amination of alkenes based on maleimides’ by Li-Wen Shen <em>et al.</em>, <em>Org. Biomol. Chem.</em>, 2025, https://doi.org/10.1039/d5ob00201j.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 16","pages":" 3967-3967"},"PeriodicalIF":2.9,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/ob/d5ob90043c?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143762764","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A near-infrared julolidine probe for visualization of mitochondrial peroxynitrite in living cells.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-01 DOI: 10.1039/d5ob00036j
Kuppan Magesh, Shu Pao Wu, Sivan Velmathi
{"title":"A near-infrared julolidine probe for visualization of mitochondrial peroxynitrite in living cells.","authors":"Kuppan Magesh, Shu Pao Wu, Sivan Velmathi","doi":"10.1039/d5ob00036j","DOIUrl":"https://doi.org/10.1039/d5ob00036j","url":null,"abstract":"<p><p>The overproduction of peroxynitrite (ONOO<sup>-</sup>) in mitochondria has been associated with various pathophysiological conditions and disorders. However, the use of fluorescent probes to visualize mitochondrial ONOO<sup>-</sup> in biological systems is limited due to their low emission wavelengths and small Stokes shifts, which present significant challenges. In this study, we designed and synthesized julolidine-based near-infrared (NIR) fluorescent probes, named JQMe and JCN, specifically to monitor mitochondrial ONOO<sup>-</sup>. Comparative photophysical studies revealed that JQMe exhibits superior properties for sensing ONOO<sup>-</sup> compared to JCN. Initially, JQMe emitted fluorescence emission at 706 nm <i>via</i> an intramolecular charge transfer (ICT) mechanism. Upon the addition of ONOO<sup>-</sup>, the NIR fluorescence emission of JQMe at 706 nm was suppressed, resulting in a rapid on-off fluorescence response within 5 minutes. JQMe exhibited high specific selectivity towards ONOO<sup>-</sup> over other competing interferents, accompanied by a colorimetric change from deep blue to colorless. Additionally, JQMe exhibited a significant Stokes shift of 106 nm and a low detection limit of 6.5 nM. The proposed sensing mechanism was validated through ESI mass spectrometry and DFT studies. Furthermore, JQMe was successfully employed to monitor both endogenous and exogenous ONOO<sup>-</sup> in living cells using inducer and inhibitor tests. Remarkably, time-dependent colocalization experiments revealed that JQMe effectively targets and reacts with mitochondrial ONOO<sup>-</sup>.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750315","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
Biocompatible silicomolybdic acid-promoted one-pot expeditious synthesis of 1,2,3-NH-triazoles.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-01 DOI: 10.1039/d5ob00298b
Danish Ansari, Manoj K Jaiswal, Mangal S Yadav, Vinay K Pandey, Mayank Singh, Vinod K Tiwari
{"title":"Biocompatible silicomolybdic acid-promoted one-pot expeditious synthesis of 1,2,3-<i>NH</i>-triazoles.","authors":"Danish Ansari, Manoj K Jaiswal, Mangal S Yadav, Vinay K Pandey, Mayank Singh, Vinod K Tiwari","doi":"10.1039/d5ob00298b","DOIUrl":"https://doi.org/10.1039/d5ob00298b","url":null,"abstract":"<p><p>The present work describes a new and practical approach for the one-pot preparation of 4-aryl-<i>NH</i>-1,2,3-triazoles and 4-glycosyl-<i>NH</i>-1,2,3-triazoles from a multicomponent reaction involving aldehydes, nitroalkanes, and sodium azide in the presence of 5 mol% of silicomolybdic acid (SMA) as a versatile and biocompatible catalyst. One-pot sequential formation of C-C and C-N bonds, high reaction yield, biocompatible nature of catalyst, easy handling, and broad substrate scope of 1,2,3-triazoles are the notable advantages of the present protocol.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750331","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
NaI-mediated α-keto-acylation of NH-sulfoximines with aryl methyl ketones.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-31 DOI: 10.1039/d5ob00166h
Parbin Rahman, Nikita Chakraborty, Bhisma K Patel, Kamal K Rajbongshi
{"title":"NaI-mediated α-keto-acylation of <i>NH</i>-sulfoximines with aryl methyl ketones.","authors":"Parbin Rahman, Nikita Chakraborty, Bhisma K Patel, Kamal K Rajbongshi","doi":"10.1039/d5ob00166h","DOIUrl":"https://doi.org/10.1039/d5ob00166h","url":null,"abstract":"<p><p>A room-temperature NaI-mediated oxidative sulfoximidation of aryl methyl ketones to synthesize α-keto-<i>N</i>-acyl sulfoximines has been disclosed. This metal- and base-free <i>NH</i>-sulfoximidation is facilitated by <i>tert</i>-butyl hydroperoxide (TBHP) as the oxidant, affording α-ketoamides with good functional group tolerance, broad substrate scope, and scalability. Mechanistic investigations indicate the intermediacy of radicals and highlight molecular oxygen's significance as the oxygen source.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750333","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
Synthesis, photochromic properties, and bioactivity of spiropyrans with electron-donating/withdrawing substituents on indoline and [2H]-chromene rings.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5ob00033e
Abir Kayal, Navjot Kaur, Mrinmoy De
{"title":"Synthesis, photochromic properties, and bioactivity of spiropyrans with electron-donating/withdrawing substituents on indoline and [2<i>H</i>]-chromene rings.","authors":"Abir Kayal, Navjot Kaur, Mrinmoy De","doi":"10.1039/d5ob00033e","DOIUrl":"https://doi.org/10.1039/d5ob00033e","url":null,"abstract":"<p><p>Photochromic molecules from the spiropyran family are renowned for their ability to undergo light-induced interconversion between a colorless spiro form and a colored merocyanine form. The photoswitching behavior of various spiropyrans has been explored earlier but the influence of electron-donating and electron-withdrawing groups on the indoline and [2<i>H</i>]-chromene rings remains unexplored. In this work, we synthesized four distinct photochromic spiropyran molecules featuring all possible combinations of electronic effects. Their photoswitching activity and switching kinetics were systematically analyzed using spectroscopic and kinetic techniques. Furthermore, the antibacterial properties of these spiropyran derivatives were evaluated to uncover potential structure-activity relationships. This study provides important insights into the design of spiropyrans with customized photochromic properties and associated bioactivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143727246","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
On the divergent reactivity of allenylstannanes generated from the O-directed free radical hydrostannation reaction of (±)-trans-3-(2-phenylcyclopropyl)prop-2-yn-1-ol. EPR evidence for the reversible addition of Ph3Sn radicals to vinyl triphenyltins.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-28 DOI: 10.1039/d4ob01847h
K Lawrence E Hale, Alistair J Fielding, Karl J Hale
{"title":"On the divergent reactivity of allenylstannanes generated from the O-directed free radical hydrostannation reaction of (±)-<i>trans</i>-3-(2-phenylcyclopropyl)prop-2-yn-1-ol. EPR evidence for the reversible addition of Ph<sub>3</sub>Sn radicals to vinyl triphenyltins.","authors":"K Lawrence E Hale, Alistair J Fielding, Karl J Hale","doi":"10.1039/d4ob01847h","DOIUrl":"10.1039/d4ob01847h","url":null,"abstract":"<p><p>(±)-<i>trans</i>-3-(2-Phenylcyclopropyl)prop-2-yn-1-ol (5) undergoes O-directed rt free radical hydrostannation with 2 equiv. of Bu<sub>3</sub>SnH or Ph<sub>3</sub>SnH in PhMe to produce the α-cyclopropyl-β-stannylvinyl radicals 26 and 27, which rapidly ring-open to give the benzylic stannylhomoallenyl radicals 28 and 29. These, in turn, react with the excess stannane that is present to provide 21 and 23 as primary reaction products. The triphenylstannylallene 23 also undergoes a competitive Ph<sub>3</sub>Sn˙ addition to its central allene carbon. This affords the allylically-stabilised radical 31c, which itself reacts with the stannane to produce (<i>Z</i>)-6-phenyl-2,3-bis(triphenylstannyl)hex-3-en-1-ol (24). EPR studies of the reaction of 5 with Ph<sub>3</sub>SnH (1 equiv.) and cat. Et<sub>3</sub>B/O<sub>2</sub> in PhMe at 250 K have failed to identify the radicals 27 and 29 in the reaction mixtures. Rather, a sharp dd is always observed whose multiplicity is consistent with it being the tris-Ph<sub>3</sub>Sn-stabilised free radical 33. The latter is suggested to arise from a reversible O-directed Ph<sub>3</sub>Sn˙ addition to 24. The radical 33 has <sup>1</sup>H<sup>β</sup> values of 1.32 mT (13.2 G) and 0.57 mT (5.7 G) and a <i>g</i> of 2.0020.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143735564","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
Synthesis of indole-linked β-cyano-enones: a pathway to indolyl-2-pyrrolones†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-27 DOI: 10.1039/D5OB00328H
Nurabul Mondal, Vidya Kumari, Danish Ali and Lokman H. Choudhury
{"title":"Synthesis of indole-linked β-cyano-enones: a pathway to indolyl-2-pyrrolones†","authors":"Nurabul Mondal, Vidya Kumari, Danish Ali and Lokman H. Choudhury","doi":"10.1039/D5OB00328H","DOIUrl":"10.1039/D5OB00328H","url":null,"abstract":"<p >Herein, we report for the first time an additive- and catalyst-free dehydrogenative multicomponent reaction of arylglyoxal, malononitrile, and indoles for the one-pot synthesis of indole-linked β-cyano-enones in DMF medium. The reaction was performed at 100 °C in DMF, forming one C–C single bond and one C<img>C double bond in a single-flask. Furthermore, we developed an efficient method for the synthesis of indolyl-2-pyrrolones having a hydroxyl group-containing chiral carbon center from the β-cyano-enones using trifluoroacetic acid and water as reaction medium. The β-cyano-enones were also further transformed into indolyl-1,2-diketones <em>via</em> a base-mediated reaction, which yielded indolyl quinoxalines upon reaction with <em>o</em>-phenylenediamine (OPD).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 16","pages":" 3913-3924"},"PeriodicalIF":2.9,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/ob/d5ob00328h?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143717697","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible-light-driven nickel-catalyzed reductive cross-coupling of benzyltrimethylammonium triflates with aryl bromides†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-26 DOI: 10.1039/D5OB00215J
Ren-Gui Tian, Mengyao Yu, Bo Ni, Muliang Zhang and Shi-Kai Tian
{"title":"Visible-light-driven nickel-catalyzed reductive cross-coupling of benzyltrimethylammonium triflates with aryl bromides†","authors":"Ren-Gui Tian, Mengyao Yu, Bo Ni, Muliang Zhang and Shi-Kai Tian","doi":"10.1039/D5OB00215J","DOIUrl":"10.1039/D5OB00215J","url":null,"abstract":"<p >Diarylmethanes are significant molecules in organic synthesis and play a vital role in pharmaceutical development. In this context, we successfully developed a visible-light-driven nickel-catalyzed cross-coupling of readily available benzyltrimethylammonium triflates with aryl bromides, enabling the direct synthesis of various diarylmethane products without the need for metal-reducing agents. Mechanistic studies have revealed that benzyl radicals, generated through photocatalysis, may serve as key intermediates, offering a novel approach to the reductive coupling of organic quaternary ammonium salts.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 16","pages":" 3841-3844"},"PeriodicalIF":2.9,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750380","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
首页 上一页 下一页 尾页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术官方微信