Organic & Biomolecular Chemistry最新文献_第2页

Recent advances in the organocatalytic synthesis of chiral C3-spiro-cyclopentaneoxindoles.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-04 DOI: 10.1039/d4ob01773k

Yan-Qing Liu, Yan Wu, Bin Li, Xue Tang, Chu Chen

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One-pot synthesis of azepine spiro[4.6]-γ-lactams by a Hantzsch-type reaction.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-04 DOI: 10.1039/d4ob01719f

Scarlet L Hopkins, Kristen T Clarke, Jack K Clegg, William J Gee

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Expeditious and environmentally benign synthesis of imidazo[4,5,1-ij]quinolines via sequential Povarov reaction/reductive cyclization.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-04 DOI: 10.1039/d4ob01588f

Laura A Heredia-Parra, Mónica C Ávila-Murillo, Cristian Ochoa-Puentes

{"title":"Expeditious and environmentally benign synthesis of imidazo[4,5,1-ij]quinolines via sequential Povarov reaction/reductive cyclization.","authors":"Laura A Heredia-Parra, Mónica C Ávila-Murillo, Cristian Ochoa-Puentes","doi":"10.1039/d4ob01588f","DOIUrl":"https://doi.org/10.1039/d4ob01588f","url":null,"abstract":"In this contribution, a novel, simple, diastereoselective and environmentally benign two-step diversity-oriented synthesis of imidazo[4,5,1-ij]quinolines is described for the first time. The synthesis of the target compounds involves a deep eutectic solvent-mediated one-pot Povarov reaction leading to the obtention of 8-nitrotetrahydroquinolines, followed by a microwave-assisted reductive cyclocondensation employing different aromatic and aliphatic aldehydes. The target compounds were obtained in up to 70% overall yield starting from commercially available o-nitroanilines, natural phenylpropanoids (trans-anethole and trans-isoeugenol) and aromatic or aliphatic aldehydes. The eutectic solvent employed in the first step was reused in four runs without observing a drastic decrease in catalytic activity, and sodium dithionite showed to be an efficient and green reducing agent for the second step. This methodology provides significant advantages in terms of synthetic and green chemistry such as mild reaction conditions, short reaction time, energy-efficiency, simple work-up procedure, low cost, scalability and utilization of renewable substrates and a reusable solvent.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142764738","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}

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One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines via BiCl₃-catalyzed and K₂S₂O₈-mediated domino annulation of β-ketosulfones and N,N-dimethylacetamide.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01681e

Meng-Yang Chang, Chun-Yi Lin

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Sustainable protocol for Cu-catalysed A³-coupling under solvent-free conditions.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01728e

Anjali Chaturvedi, Vishal Sharma, Ravindra K Rawal, Manpreet Singh, Virender Singh

引用次数: 0

Visible light-induced PPh₃/MI-promoted δ-C(sp³)-H chlorination and cyclization with N-chloro-arylsulfonamides via EDA complexes.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01484g

Xiaotao Qin, Hui Liu, Jinkai Hu, Chenglei Yang, Ao-Tong Shi, Qing-Long Lv, Jinhui Yang, Dianjun Li

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Facile Ru-catalysed synthesis of quinazolin-4(3H)-ones by tandem cyclization of 2-nitrobenzonitrile and alcohol derivatives under air.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01786b

Ban Van Phuc, Tien Dat Nguyen, Nguyen T Minh Tuan, Phuong Anh Dao, Phan T Thao Vy, Hien Nguyen, Ngoc Tuan Nguyen, Quoc Anh Ngo, Tran Quang Hung, Tuan Thanh Dang

引用次数: 0

Homophenylalanine-derived benzo[1,4]diazepine-2,5-diones are strong bacterial quorum sensing inhibitors.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01734j

Manuel Einsiedler, Sanja Š Bogojević, Dušan Milivojević, Sandra Vojnovic, Miloš K Milčić, Veselin Maslak, Anke Matura, Tobias A M Gulder, Jasmina Nikodinovic-Runic

{"title":"Homophenylalanine-derived benzo[1,4]diazepine-2,5-diones are strong bacterial quorum sensing inhibitors.","authors":"Manuel Einsiedler, Sanja Š Bogojević, Dušan Milivojević, Sandra Vojnovic, Miloš K Milčić, Veselin Maslak, Anke Matura, Tobias A M Gulder, Jasmina Nikodinovic-Runic","doi":"10.1039/d4ob01734j","DOIUrl":"https://doi.org/10.1039/d4ob01734j","url":null,"abstract":"Benzo[1,4]diazepines show a large diversity of biological activities and are still commonly used as medications against a broad range of diseases. Within our research in the field of chemo-enzymatic alkaloid synthesis, we developed a synthetic route towards close structural relatives, namely benzo[1,4]diazepine-2,5-diones. Possible antimicrobial activities of these substances are barely known up to date. We thus screened a selection of 21 of these compounds and discovered their ability to interfere with bacterial communication (quorum sensing, QS). Derivatisation of the respective substances by a refined synthetic route resulted in a generation of 9 congeners with drastically enhanced activity, setting the stage for the application of benzo[1,4]diazepine-2,5-diones, a formerly under-investigated compound class, as QS modulators. Molecular docking experiments were performed to evaluate potential protein interaction partners - LuxP, LasR, AbaI, and RhlR - which are involved in QS. The results of the docking calculations show a high energy binding site for three analogues, 5q, 15a and 15b, in the autoinducer binding-pocket of LasR, with the position of a fluorine substituent on the diazepine core structure determining the exact spatial orientation of the compounds.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142764806","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

Dynamic covalent bonding (DCB): the bond lability of alkoxyamines as drugs against Schistosoma mansoni and Plasmodium falciparum.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01644k

Ange W Embo-Ibouanga, Michel Nguyen, Lucie Paloque, Jean-Patrick Joly, Raphaël Bikanga, Jean-Michel Augereau, Anne Robert, Gérard Audran, Philippe Mellet, Jérôme Boissier, Françoise Benoit-Vical, Sylvain R A Marque

引用次数: 0

Halogen bonding accelerated aerobic dehydrogenative aromatization for 4-aminoquinoline preparation.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-12-03 DOI: 10.1039/d4ob01700e

Zikun Yao, Pan Li, Fei Chen, Jiuwei Nie, Hui Wang, Lei Tang, Yuanyong Yang

{"title":"Halogen bonding accelerated aerobic dehydrogenative aromatization for 4-aminoquinoline preparation.","authors":"Zikun Yao, Pan Li, Fei Chen, Jiuwei Nie, Hui Wang, Lei Tang, Yuanyong Yang","doi":"10.1039/d4ob01700e","DOIUrl":"https://doi.org/10.1039/d4ob01700e","url":null,"abstract":"This study presents a highly efficient method for 4-aminoquinoline derivative preparation under transition metal-free conditions. The process involves an aerobic oxidative dehydrative coupling of 2,3-dihydroquinolin-4(1H)-ones with various amines, including ammonia, resulting in high yields of the desired products. The method is also applicable to substituted 4-aminoquinoline derivative construction through a cyclization/dehydrative coupling cascade process starting from 2'-amino chalcones. Mechanistic studies reveal that iodine (I2) is consumed to produce 3-iodoquinolin-4-ol, which acts as a true catalyst with high catalytic efficacy (as low as 0.5 mol%). The presence of halogen bonding is critical in the inter-molecular transfer hydrogenation process to generate inactive quinolin-4-ol. Subsequently, using air/oxygen as the terminal oxidant, the iodine anion was oxidized to I2 to regenerate the 3-iodoquinolin-4-ol from quinolin-4-ol in the catalytic cycle. Key benefits of this methodology include its simplicity, transition metal-free conditions, environmentally-benign oxidant, and high atom economy, making it a valuable approach for synthesizing medicinally significant 4-aminoquinoline derivatives.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142764770","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