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Synthesis of Chiral β-Trifluoromethyl-β-Amino Acid Derivatives in Aqueous Medium
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1002/ajoc.202400812
Sasirome Racochote, Prof. Dr. Chutima Kuhakarn, Dr. Pawaret Leowanawat, Dr. Khetpakorn Chakarawet, Prof. Dr. Vichai Reutrakul, Dr. Darunee Soorukram
{"title":"Synthesis of Chiral β-Trifluoromethyl-β-Amino Acid Derivatives in Aqueous Medium","authors":"Sasirome Racochote,&nbsp;Prof. Dr. Chutima Kuhakarn,&nbsp;Dr. Pawaret Leowanawat,&nbsp;Dr. Khetpakorn Chakarawet,&nbsp;Prof. Dr. Vichai Reutrakul,&nbsp;Dr. Darunee Soorukram","doi":"10.1002/ajoc.202400812","DOIUrl":"https://doi.org/10.1002/ajoc.202400812","url":null,"abstract":"<p>A practical synthesis of chiral <i>β</i>-trifluoromethyl-<i>β</i>-amino acids is reported by using water as a reaction medium to facilitate the diastereoselective aza-Michael addition of aromatic amines to chiral <i>β</i>-trifluoromethyl-<i>α</i>,<i>β</i>-unsaturated oxazolidinone. A variety of aromatic amines could serve as a suitable nucleophile that readily undergo nucleophilic conjugate addition at ambient temperature to provide the corresponding <i>β</i>-trifluoromethyl-<i>β</i>-amino acid derivatives in excellent combined yields (up to 97 %) with moderate to good diastereoselectivities (up to 3 : 1). Being complementary to the precedent methods, this work offers the advantages, e. g., a green and environmentally friendly reaction medium, a stable and readily synthesized chiral starting material, and a simple and practical operation providing enantioenriched <i>β</i>-trifluoromethyl-<i>β</i>-amino acids which are found major applications in advanced organic synthesis and medicinal research field.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846044","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Three New Strategies to the Synthesis Of Structurally Diverse Dipyrrolobenzodiazepines. Bioactivity Evaluation
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-05 DOI: 10.1002/ajoc.202500018
Anna D. Zinoveva, Valeria A. Podchufarova, Tatiana N. Borisova, Anton P. Novikov, Olga V. Levitskaya, Alexander A. Titov, Yana I. Gaponenko, Tuyet Anh Dang Thi, Dao Thi Nhung, Le Tuan Anh, Tuyen Van Nguyen, Alexey V. Varlamov, Leonid G. Voskressensky
{"title":"Three New Strategies to the Synthesis Of Structurally Diverse Dipyrrolobenzodiazepines. Bioactivity Evaluation","authors":"Anna D. Zinoveva,&nbsp;Valeria A. Podchufarova,&nbsp;Tatiana N. Borisova,&nbsp;Anton P. Novikov,&nbsp;Olga V. Levitskaya,&nbsp;Alexander A. Titov,&nbsp;Yana I. Gaponenko,&nbsp;Tuyet Anh Dang Thi,&nbsp;Dao Thi Nhung,&nbsp;Le Tuan Anh,&nbsp;Tuyen Van Nguyen,&nbsp;Alexey V. Varlamov,&nbsp;Leonid G. Voskressensky","doi":"10.1002/ajoc.202500018","DOIUrl":"https://doi.org/10.1002/ajoc.202500018","url":null,"abstract":"<p>Simple and efficient strategies have been developed for the synthesis of three structurally diverse dipyrrolo[1,2-<i>a</i> : 2′,1′-<i>c</i>][1,4]benzodiazepine (DPBD) derivatives. Firstly, two-component reaction between 4-aroylpyrrolo[1,2-<i>a</i>][1,4]benzodiazepines and electron-deficient internal alkynes in different conditions was applied to obtain isomeric geminal and vicinal DPBDs (<i><b>gem</b></i> and <i><b>vic</b></i>). Secondly, multicomponent synthesis from 2-pyrrolylbenzylamine, arylglyoxal monohydrates and same alkynes led to the formation of other vicinal DPBDs (<i><b>vic</b></i><b>’</b>). These transformations could be conducted under mild and metal-free conditions to provide a number of dipyrrolo[1,2-<i>a</i> : 2′,1′-<i>c</i>][1,4]benzodiazepine derivatives in moderate to good yields. The <i>in vitro</i> biological activity of title compounds have been tested. Further physicochemical and pharmacokinetic computations also demonstrated the drug-like characteristics of synthesized compounds. The cytotoxic activity IC<sub>50</sub> 27.59 (KB cell culture) as well as molecular docking with bromodomain-containig protein 4 (BRD4) indicated the importance of dipyrrolobenzodiazepine moieties in the development of potential anticancer agents.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845987","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Two-Pot Synthesis of Indolizinoindole Derivatives via Lewis Acid-Mediated Intramolecular Regioselective Cyclization of 3-Acylpyrroles
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-04 DOI: 10.1002/ajoc.202400733
Mamta, Imtiyaz Ahmad Shah, Mainika Verma, Prof. Krishnan Rangan, Prof. Eldhose Iype, Prof. Bharti Khungar, Prof. Indresh Kumar
{"title":"Two-Pot Synthesis of Indolizinoindole Derivatives via Lewis Acid-Mediated Intramolecular Regioselective Cyclization of 3-Acylpyrroles","authors":"Mamta,&nbsp;Imtiyaz Ahmad Shah,&nbsp;Mainika Verma,&nbsp;Prof. Krishnan Rangan,&nbsp;Prof. Eldhose Iype,&nbsp;Prof. Bharti Khungar,&nbsp;Prof. Indresh Kumar","doi":"10.1002/ajoc.202400733","DOIUrl":"https://doi.org/10.1002/ajoc.202400733","url":null,"abstract":"<p>A two-pot method has been developed to access indolizino[8,7-<i>b</i>]indole derivatives through Lewis acid-mediated regioselective C5-cyclization of 3-acylpyrrole prepared from the feedstock materials. The overall reaction proceeds through amine-catalyzed direct aldol reaction/Paal-Knorr reaction/oxidation between succinaldehyde, aromatic aldehyde, and tryptamine in a sequential multicomponent fashion for N-alkyl pyrrole followed by dearomative cyclization. A series of substituted indolizino[8,7-<i>b</i>]indoles have been prepared with good yields and excellent regioselectivity.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400733","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845941","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Synthesis of Highly Functionalized Tetrahydropyridines by Ring Opening of [3.3.1]-Heterobicyclic Compounds with Grignard Reagents
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-04 DOI: 10.1002/ajoc.202400743
Lucrezia Margherita Comparini, Giovanni Turchi, Francesca Sardelli, Lucilla Favero, Valeria Di Bussolo, Sebastiano Di Pietro, Mauro Pineschi
{"title":"Synthesis of Highly Functionalized Tetrahydropyridines by Ring Opening of [3.3.1]-Heterobicyclic Compounds with Grignard Reagents","authors":"Lucrezia Margherita Comparini,&nbsp;Giovanni Turchi,&nbsp;Francesca Sardelli,&nbsp;Lucilla Favero,&nbsp;Valeria Di Bussolo,&nbsp;Sebastiano Di Pietro,&nbsp;Mauro Pineschi","doi":"10.1002/ajoc.202400743","DOIUrl":"https://doi.org/10.1002/ajoc.202400743","url":null,"abstract":"<p>We herein report our study about the ring opening of 1,3-diaza-4-oxa-[3.3.1]-nonene derivatives with organometallic reagents leveraging on their inherent ring strain and presence of reactive functionalities. The ring-opening occurs with Grignard reagents at the carbon bearing the two nitrogen atoms affording unconventional functionalized <i>trans</i>-2,3-disubstituted 1,2,3,6-tetrahydropyridines that are important structural frameworks due to their synthetic versatility and presence in bioactive molecules. The possibility to prepare enantioenriched tetrahydropyridines was also formally explored with success. A computational DFT study points to the formation of a transient iminium ion intermediate in which the coordination of magnesium to the oxygen of the carbonyl and the N−O endocyclic oxygen promotes the ring-opening process at the <i>gem-</i>diamine carbon atom.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845983","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Switchable Site-Selectivite Direct Acetoxylation of Pyrazolones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-03 DOI: 10.1002/ajoc.202400808
Tanakorn Kittikool, Tarm Viriyanukul, Kunita Phakdeeyothin, Sirilata Yotphan
{"title":"Switchable Site-Selectivite Direct Acetoxylation of Pyrazolones","authors":"Tanakorn Kittikool,&nbsp;Tarm Viriyanukul,&nbsp;Kunita Phakdeeyothin,&nbsp;Sirilata Yotphan","doi":"10.1002/ajoc.202400808","DOIUrl":"https://doi.org/10.1002/ajoc.202400808","url":null,"abstract":"<p>Site-selective direct acetoxylation of pyrazolones was accomplished by utilizing an easy-to-handle (diacetoxyiodo)benzene (PIDA) as the sole acetoxylating reagent. In the presence of Pd(OAc)<sub>2</sub> catalyst, the 4-acetoxylated pyrazolone product was exclusively formed. Meanwhile, in the absence of Pd(OAc)<sub>2</sub>, the pyrazolone methyl acetate product was obtained over the C<i>sp</i><sup><i>2</i></sup>−H bond functionalization. Both approaches have been successfully applied to various pyrazolone substrates, giving the corresponding products in moderate to high yields under mild conditions.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845934","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Synthesis of Chiral Sulfimides 手性亚硫酰亚胺的不对称合成
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-03 DOI: 10.1002/ajoc.202400765
Saori Tsuzuki, Taichi Kano
{"title":"Asymmetric Synthesis of Chiral Sulfimides","authors":"Saori Tsuzuki,&nbsp;Taichi Kano","doi":"10.1002/ajoc.202400765","DOIUrl":"https://doi.org/10.1002/ajoc.202400765","url":null,"abstract":"<p>Chiral sulfimides (sulfilimines), aza-analogues of sulfoxides, are valuable compounds in organic synthesis and medicinal chemistry. They show unique biological properties, and the stereochemistry of the sulfur atom affects their biological activity. This mini-review highlights the development in asymmetric synthesis of chiral sulfimides over the last hundred years.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845797","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Optically Active Tolane-Stacked Molecules Based on Planar Chiral [2.2]Paracyclophanes
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-03 DOI: 10.1002/ajoc.202400624
Shun Yukimoto, Dr. Ryo Inoue, Takuma Ito, Prof. Yasuhiro Morisaki
{"title":"Synthesis of Optically Active Tolane-Stacked Molecules Based on Planar Chiral [2.2]Paracyclophanes","authors":"Shun Yukimoto,&nbsp;Dr. Ryo Inoue,&nbsp;Takuma Ito,&nbsp;Prof. Yasuhiro Morisaki","doi":"10.1002/ajoc.202400624","DOIUrl":"https://doi.org/10.1002/ajoc.202400624","url":null,"abstract":"<p>In this study, optically active compounds were synthesized by stacking diarylacetylenes with two benzene rings and an ethynylene (tolane derivatives) using planar chiral [2.2]paracyclophanes. The compounds with carboxy groups formed one-dimensional zig-zag structures through hydrogen bonds in the crystals, with three hydrogen-bonded chains bundled to construct a one-handed triple helix. All compounds prepared in this study exhibited circularly polarized luminescence properties with good anisotropy factors.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845935","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Polyfunctional Indazoles via Novel Rearrangement of Isatin Derivatives
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-02 DOI: 10.1002/ajoc.202400656
Elena Bezsonova, Viktor Tafeenko, Sergey Sosonyuk, Natalia Lozinskaya
{"title":"Synthesis of Polyfunctional Indazoles via Novel Rearrangement of Isatin Derivatives","authors":"Elena Bezsonova,&nbsp;Viktor Tafeenko,&nbsp;Sergey Sosonyuk,&nbsp;Natalia Lozinskaya","doi":"10.1002/ajoc.202400656","DOIUrl":"https://doi.org/10.1002/ajoc.202400656","url":null,"abstract":"<p>In this work we present a new method for indazole synthesis through the unexpected rearrangement of various 7-nitroisatins during the reaction with hydrazine hydrate. The new pyrazole cycle is formed via direct metal-free C−H amination. We demonstrate the limitations of the discovered approach and several accessible methods for functionalization of the compounds to obtain novel indazole derivatives.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845932","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Chiral Natural Products With Anti-Plasmodium Activity Identified from the East African Flora From 2000 to 2023
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-02 DOI: 10.1002/ajoc.202400494
Dr. Samuel Gachuhi, Prof. Yaouba Souaibou, Dr. Lonwabo Ngodwana, Dr. Lebusetsa Taleli
{"title":"Chiral Natural Products With Anti-Plasmodium Activity Identified from the East African Flora From 2000 to 2023","authors":"Dr. Samuel Gachuhi,&nbsp;Prof. Yaouba Souaibou,&nbsp;Dr. Lonwabo Ngodwana,&nbsp;Dr. Lebusetsa Taleli","doi":"10.1002/ajoc.202400494","DOIUrl":"https://doi.org/10.1002/ajoc.202400494","url":null,"abstract":"<p>For more than half a century, significant strides have been taken to reduce the incidence of malaria, but nearly half of the world‘s population is still at risk of malaria infection. Development of parasite resistance to antimalarial drugs remains a medical challenge that requires identification and development of novel drug-like anti-plasmodial leads that are active against drug resistant parasites. The benefits of chiral natural product (NPs) as anti-<i>Plasmodium</i> drugs can be traced back to Quinine. To date, the importance of stereogenic centers in drug discovery continues to influence clinical pharmacology of various clinical candidates. This review retrospectively examines chiral natural product anti-<i>Plasmodium</i> agents from the East African flora published between year 2000 and 2023. The intention is to identify promising leads that could be ideal starting points for development of the next generation of antimalarial drugs.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845933","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Ultrasmall Fe3O4 Nanoparticles on ZrO2 as Catalysts for CO2 Hydrogenation to Lower Olefins
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI: 10.1002/ajoc.202400379
Huda S. Alghamdi , Mohammed A. Sanhoob , Afnan M. Ajeebi , Md. Abdul Aziz , M. Nasiruzzaman Shaikh , Lee Hwei Voon
{"title":"Ultrasmall Fe3O4 Nanoparticles on ZrO2 as Catalysts for CO2 Hydrogenation to Lower Olefins","authors":"Huda S. Alghamdi ,&nbsp;Mohammed A. Sanhoob ,&nbsp;Afnan M. Ajeebi ,&nbsp;Md. Abdul Aziz ,&nbsp;M. Nasiruzzaman Shaikh ,&nbsp;Lee Hwei Voon","doi":"10.1002/ajoc.202400379","DOIUrl":"10.1002/ajoc.202400379","url":null,"abstract":"<div><div>Organic synthesis presents significant opportunities for converting the abundant and hazardous carbon dioxide (CO<sub>2</sub>) in the atmosphere into a more sustainable carbon source. To reduce the carbon footprint, we explored the direct hydrogenation of CO<sub>2</sub> to lower (C<sub>2‐4</sub><sup>=</sup>) olefins using various catalysts composed of ZrO<sub>2</sub>‐supported alkali‐metal‐promoted superparamagnetic iron oxide nanoparticles (SPIONs; Fe<sub>3</sub>O<sub>4</sub>). These catalysts are notable for their straightforward preparation; we employed a cost‐effective dry‐mixing method to create a range of alkali metal‐doped SPIONs supported on ZrO<sub>2</sub>. Results showed that the strong interactions between Fe<sub>3</sub>O<sub>4</sub> and the ZrO<sub>2</sub> support enhanced CO<sub>2</sub> hydrogenation performance compared to other forms.. Under optimal conditions – using a gas hourly space velocity (GHSV) of 4500 mL/h/g<sub>cat.</sub> and a feed ratio of H<sub>2</sub>:CO<sub>2</sub>=3 : 1 – this catalyst achieved over 22 % CO<sub>2</sub> conversion and high selectivity for light (C<sub>2–4</sub><sup>=</sup>) olefins at 30 bar and 375 °C, with 30 wt% Fe<sub>3</sub>O<sub>4</sub> loading on ZrO<sub>2</sub> and 2 wt% K promoter. We also investigated several variables, including alkali metal concentration, iron content, reaction conditions, and catalyst stability over 96 hours.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400379"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423702","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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