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C−H Methylthiolation/d3‐Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400639
Haofeng Shi , Fengxia Sun , Jialiang Wu , Jiaxin He , Yuli Sun , Yunfei Du
{"title":"C−H Methylthiolation/d3‐Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction","authors":"Haofeng Shi ,&nbsp;Fengxia Sun ,&nbsp;Jialiang Wu ,&nbsp;Jiaxin He ,&nbsp;Yuli Sun ,&nbsp;Yunfei Du","doi":"10.1002/ajoc.202400639","DOIUrl":"10.1002/ajoc.202400639","url":null,"abstract":"<div><div>The reaction of a series of pyrazole derivatives with DMSO/ ‐DMSO‐<em>d<sub>6</sub></em> and thionyl chloride conveniently afforded the 4‐thiolated pyrazole products under metal‐free conditions. This C−H functionalization/elelctrophilic thiolation process is postulated to involve the <em>in situ</em> generation of the electrophilic hypochlorothioite <em>via</em> interrupted Pummerer reaction, followed with the electrophilic methylthiolation of pyrazole skeleton.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400639"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622551","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
Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400617
Fatemeh Doraghi , Shahab Kermaninia , Hadi Afaridoun , Bagher Larijani , Mohammad Mahdavi
{"title":"Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes","authors":"Fatemeh Doraghi ,&nbsp;Shahab Kermaninia ,&nbsp;Hadi Afaridoun ,&nbsp;Bagher Larijani ,&nbsp;Mohammad Mahdavi","doi":"10.1002/ajoc.202400617","DOIUrl":"10.1002/ajoc.202400617","url":null,"abstract":"<div><div>Transition metal‐catalyzed transformations of bridged‐ring bicyclic alkenes have emerged as an interesting area of synthetic chemistry in the last two decades. Due to their multiple points of reactivity, bicyclic alkenes, especially <em>oxa</em>/<em>aza</em>‐bicyclic alkenes, can participate in a variety annulation/functionalization reactions catalyzed by transition metals. In this review, a wide range of transition metal‐catalyzed C−H activation/addition of bicyclic alkenes with nucleophiles is described.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400617"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622552","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
Indenoindenes, Indenoindoles, and Indenobenzofurans via the Interrupted iso‐Nazarov Reaction
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400655
Sineenart Attanonchai , Kasam Poonswat , Prof. Dr. Somsak Ruchirawat , Dr. Poonsakdi Ploypradith
{"title":"Indenoindenes, Indenoindoles, and Indenobenzofurans via the Interrupted iso‐Nazarov Reaction","authors":"Sineenart Attanonchai ,&nbsp;Kasam Poonswat ,&nbsp;Prof. Dr. Somsak Ruchirawat ,&nbsp;Dr. Poonsakdi Ploypradith","doi":"10.1002/ajoc.202400655","DOIUrl":"10.1002/ajoc.202400655","url":null,"abstract":"<div><div>The cascade carbocation cyclization (CCC) of the secondary benzylic, or the benzhydryl, carbocation by the 2‐indene, 2/3‐indole, or 2/3‐benzofuran followed by the intermolecular nucleophilic addition by H‐/allyl‐silane or electron‐rich arenes, also classifiable as the interrupted <em>iso</em>‐Nazarov reaction, provided the corresponding indane‐fused indane/indole/benzofuran scaffolds. The initial CCC forged the <em>trans</em> relationship at the two newly formed adjacent stereogenic centers while the latter provided the selective <em>cis</em> stereocontrol at the new ring junction. Starting from achiral alcohols, the reaction sequence furnished the oxygen/nitrogen‐containing indane fused‐ring tetracyclic systems in moderate to good yields with excellent stereoselectivity on all three contiguous chiral centers.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400655"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622343","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 a Bis‐Boron/Sulfur Doped Ullazine and Direct Comparison with Its Boron/Nitrogen and Boron/Oxygen Analogues
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400637
Ruijun Jiang , Tingting Qin , Yiping Wang , Huicong Cui , Yanping Shi , Lei Zhang , Dr. Xuguang Liu
{"title":"Synthesis of a Bis‐Boron/Sulfur Doped Ullazine and Direct Comparison with Its Boron/Nitrogen and Boron/Oxygen Analogues","authors":"Ruijun Jiang ,&nbsp;Tingting Qin ,&nbsp;Yiping Wang ,&nbsp;Huicong Cui ,&nbsp;Yanping Shi ,&nbsp;Lei Zhang ,&nbsp;Dr. Xuguang Liu","doi":"10.1002/ajoc.202400637","DOIUrl":"10.1002/ajoc.202400637","url":null,"abstract":"<div><div>Ullazine, a typical polycyclic aromatic hydrocarbon with a 14 π‐electron nitrogen‐containing core, has garnered significant attention due to its excellent performance in optoelectronics applications. Integration of heteroatoms into the frameworks of polycyclic aromatic hydrocarbons is a well‐established strategy for modifying molecular characteristics and functionalities. In this study, heteroatom‐doped ullazine congener <strong>Bis‐BS‐U</strong> containing two boron‐sulfur bonds was synthesized. The structures and properties of <strong>Bis‐BS‐U</strong> were systematically compared to those of the previously reported bis‐boron/nitrogen doped ullazine (<strong>Bis‐BN‐U</strong>) and bis‐boron/oxygen doped ullazine (<strong>Bis‐BO‐U</strong>). Notably, the absorption and fluorescence spectra of <strong>Bis‐BS‐U</strong> exhibited a pronounced red shift relative to those of <strong>Bis‐BN‐U</strong> and <strong>Bis‐BO‐U</strong>. Theoretical calculations suggest that the boron/sulfur six‐member ring in <strong>Bis‐BS‐U</strong> exhibits very weak antiaromaticity. Moreover, the fluorescence intensity of <strong>Bis‐BS‐U</strong> showed an initial increase upon addition of Hg<sup>2+</sup>, followed by gradual decrease over time. This study expands the family of ullazine and provides valuable insights for the future development of heteroatom‐doped ullazines.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400637"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622449","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
One‐Pot Synthesis of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400682
Norio Sakai , Takahiro Yokoyama , Kento Ishida
{"title":"One‐Pot Synthesis of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes","authors":"Norio Sakai ,&nbsp;Takahiro Yokoyama ,&nbsp;Kento Ishida","doi":"10.1002/ajoc.202400682","DOIUrl":"10.1002/ajoc.202400682","url":null,"abstract":"<div><div>We demonstrated that indium bromide, a trivalent indium compound with strong tolerance toward various coordination functional groups, can be used as a sole promotor to effectively promote the hydrohydrazination of a variety of <em>N</em>‐phenylhydrazines with aromatic/aliphatic alkynes and the subsequent [3,3]‐sigmatropic reaction of the hydrazone intermediate, leading to the one‐pot preparation of various poly‐substituted indole derivatives. Notably, the initial hydrohydrazination proceeded in a Markovnikov‐type manner and showed high regioselectivity, with the hydrohydrazination of arylalkynes affording only 2‐arylindole derivatives. Therefore, our findings provide a facile and practical one‐pot process for the synthesis of polysubstituted indole derivatives from various phenylhydrazines and aromatic/aliphatic alkynes using only one promotor.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400682"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400682","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622637","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
C–Centered Radicals: Generation, Detection, Stability and Perspectives
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400686
Dr. Archana Velloth , Piyush Kumar , Shabana Butt , Dr. Sugumar Venkataramani
{"title":"C–Centered Radicals: Generation, Detection, Stability and Perspectives","authors":"Dr. Archana Velloth ,&nbsp;Piyush Kumar ,&nbsp;Shabana Butt ,&nbsp;Dr. Sugumar Venkataramani","doi":"10.1002/ajoc.202400686","DOIUrl":"10.1002/ajoc.202400686","url":null,"abstract":"<div><div><em>C–</em>Centered radicals are one of the classical reactive intermediates that have shown enormous utility in organic synthesis. Besides homolytic bond cleavages, the advancements of electron transfer‐based photoredox and electroredox processes are popular choices for their generation and synthetic explorations. Considering the widespread attention and versatility of <em>C</em>‐centered radicals in several fields, a systematic understanding of structural, stability, and reactivity aspects is crucial for the further development and futuristic applications of radical chemistry. In this regard, several topics pertaining to the generation, detection, and studies relevant to radical chemistry in general and thermodynamic and kinetic stability of the <em>C</em>‐centered radicals specifically, with a major emphasis on physical organic chemistry aspects, are presented. Besides portraying the factors governing their stability and reactivity, this contribution also discusses their challenges and perspectives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400686"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622727","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
A Review on Use of Electrolytes in Catalytic/ Sub‐Stoichiometric Amounts in Electro‐Organic Synthesis: A Much Greener Approach
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400307
Dr. Toreshettahally R. Swaroop , Dr. Rajaghatta N. Suresh , Dr. Muddegowda Umashankara , Dr. Kanchugarakoppal S. Rangappa
{"title":"A Review on Use of Electrolytes in Catalytic/ Sub‐Stoichiometric Amounts in Electro‐Organic Synthesis: A Much Greener Approach","authors":"Dr. Toreshettahally R. Swaroop ,&nbsp;Dr. Rajaghatta N. Suresh ,&nbsp;Dr. Muddegowda Umashankara ,&nbsp;Dr. Kanchugarakoppal S. Rangappa","doi":"10.1002/ajoc.202400307","DOIUrl":"10.1002/ajoc.202400307","url":null,"abstract":"<div><div>In this review, we have discussed the various types of organic electrochemical reactions which use catalytic/sub‐stoichiometric amount of inorganic and/or organic salts as electrolytes. We have also presented the plausible mechanism of each electro‐organic reaction. This review article highlights notable examples of electro‐organic synthesis published from 2000 to 2023.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400307"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622705","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 2H‐1,4‐Oxazin‐3(4H)‐One Utilizing Umpolung Reaction to α‐Hydrazonoketone
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400698
Dr. Isao Mizota , Keiji Oshima , Nozomi Hoshiai , Ayaki Yamamoto , Masaki Mitani , Rabbia Batool , Prof. Dr. Bo‐Tau Liu , Prof. Dr. Makoto Shimizu
{"title":"Synthesis of 2H‐1,4‐Oxazin‐3(4H)‐One Utilizing Umpolung Reaction to α‐Hydrazonoketone","authors":"Dr. Isao Mizota ,&nbsp;Keiji Oshima ,&nbsp;Nozomi Hoshiai ,&nbsp;Ayaki Yamamoto ,&nbsp;Masaki Mitani ,&nbsp;Rabbia Batool ,&nbsp;Prof. Dr. Bo‐Tau Liu ,&nbsp;Prof. Dr. Makoto Shimizu","doi":"10.1002/ajoc.202400698","DOIUrl":"10.1002/ajoc.202400698","url":null,"abstract":"<div><div>2<em>H</em>‐1,4‐Oxazin‐3(4<em>H</em>)‐One Derivatives Are Known to Exhibit a Wide Range of Biological Activities Such as Antifungal, Anticancer, as Receptor Antagonists and Potassium Channel Modulators. In This Report, We Describe That α‐Hydrazonoketone Is an Appropriate Substrate for the Umpolung Reaction and a Promising Candidate for the Synthesis of 2<em>H</em>‐1,4‐Oxazine‐3(4<em>H</em>)‐Ones. Notably, Umpolung <em>N</em>‐Methylation for α‐Hydrazonoketone Proceeded Quantitatively in a Mild and Extremely Short Reaction Time, Which Has Been Difficult to Achieve in the Conventional Reactions. Moreover, We Also Developed Tandem Umpolung Reaction/Reduction/<em>N‐</em>Acyl<em>‐O</em>‐Alkylation to Afford 2<em>H</em>‐1,4‐Oxazin‐3(4<em>H</em>)‐Ones in High Yield in the Presence of Chloroacetyl Chloride.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400698"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400698","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622286","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
Oxirane‐Driven Cascade Transformations of 5‐Arylidene‐Thiazolidine‐2,4‐Diones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400645
Dr. Alexander Yu. Simonov , Dr. Alexey A. Panov , Dr. Andrei V. Churakov , Prof. Dr. Vladimir I. Polshakov , Prof. Dr. Igor B. Levshin
{"title":"Oxirane‐Driven Cascade Transformations of 5‐Arylidene‐Thiazolidine‐2,4‐Diones","authors":"Dr. Alexander Yu. Simonov ,&nbsp;Dr. Alexey A. Panov ,&nbsp;Dr. Andrei V. Churakov ,&nbsp;Prof. Dr. Vladimir I. Polshakov ,&nbsp;Prof. Dr. Igor B. Levshin","doi":"10.1002/ajoc.202400645","DOIUrl":"10.1002/ajoc.202400645","url":null,"abstract":"<div><div>The reaction of thiazolidine‐2,4‐diones (TZDs) with oxiranes has been thoroughly investigated. For the first time, it has been observed that 5‐arylidene‐TZD derivatives can undergo transformation into 6‐substituted 1,4‐oxathian‐2‐ones. Additionally, it has been demonstrated that certain 3‐substituted 5‐arylidene‐TZDs can convert to 1,4‐oxathian‐2‐ones and oxazolidines upon reaction with oxiranes, confirming that the process follows a cascade mechanism. Several factors have been found to influence the reaction‘s outcome, including the amount of oxirane, the presence of a base, and solvent polarity. It has been determined that dimethylformamide (DMF) is essential for the reaction to proceed efficiently. Furthermore, the critical role of the benzylidene group in facilitating the reaction has been confirmed. An unusual hydrogen bond between the ortho‐hydrogens of the phenyl group and the sulfur atom of the thiazolidine ring, observed via NMR spectroscopy, highlights the sulfur atom‘s strong electron‐accepting properties, which play a key role in the observed transformations.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400645"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622349","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 Bridged and Fused Tetracycles via Rhodium‐Catalyzed C−H Allylation/Cycloaddition of Azomethine Imines with MBH Adducts and Allyl Acetates
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400646
Yang Sun , Yiyan Wang , Lijun Zhang , Rui Zhong , Hui Wang
{"title":"Synthesis of Bridged and Fused Tetracycles via Rhodium‐Catalyzed C−H Allylation/Cycloaddition of Azomethine Imines with MBH Adducts and Allyl Acetates","authors":"Yang Sun ,&nbsp;Yiyan Wang ,&nbsp;Lijun Zhang ,&nbsp;Rui Zhong ,&nbsp;Hui Wang","doi":"10.1002/ajoc.202400646","DOIUrl":"10.1002/ajoc.202400646","url":null,"abstract":"<div><div>A rhodium‐catalyzed cascade C−H allylation combined with <em>exo</em>‐ and <em>endo</em>‐type [3+2] dipolar cycloaddition of aryl azomethine imines with Morita‐Baylis‐Hillman (MBH) adducts and allyl acetates is described. This process, which is operationally simple and proceeds efficiently in air and moisture under neat conditions, facilitates diverse bridged and fused tetracycles as single diastereomers. The reaction showcases a broad substrate scope and good functional group compatibility. Furthermore, its practicality is further demonstrated through successful scale‐up and synthetic applications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400646"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622355","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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