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Journal of Heterocyclic Chemistry最新文献

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Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)-Catalyzed Cycloisomerization and Intramolecular Ullmann-Type Coupling Reaction 通过金(I)催化的环异构化和分子内乌尔曼型偶联反应简易合成偶氮菲类生物碱大黄素
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-09-02 DOI: 10.1002/jhet.4889
Eunyeong Kim, Young Taek Han
{"title":"Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)-Catalyzed Cycloisomerization and Intramolecular Ullmann-Type Coupling Reaction","authors":"Eunyeong Kim,&nbsp;Young Taek Han","doi":"10.1002/jhet.4889","DOIUrl":"10.1002/jhet.4889","url":null,"abstract":"<div>\u0000 \u0000 <p>A concise and efficient synthesis of the γ-lactam-fused azaphenanthrene alkaloid eupolauramine has been achieved. The key feature of the synthesis involves Au(I)-catalyzed cycloisomerization of <i>N</i>-naphthyl aminobutynamide intermediate and subsequent intramolecular Ullmann-type coupling reaction. This study clearly demonstrated the usefulness of coinage metal-catalyzed cycloisomerization strategy in the construction of architecturally sophisticated pyridine-fused heterocyclic scaffolds.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1622-1626"},"PeriodicalIF":2.0,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142209410","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 Novel 6 H-Furo[3,2-e]Indole Derivatives via One-Pot Three Component Reactions 通过一锅三组份反应合成新型 6H-呋喃并[3,2-e]吲哚衍生物
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-08-28 DOI: 10.1002/jhet.4883
Dan-Dan Wan, Shuang-Ling Wu, Jia-Yan Liu, Dong-Sheng Chen
{"title":"Synthesis of Novel 6\u0000 H-Furo[3,2-e]Indole Derivatives via One-Pot Three Component Reactions","authors":"Dan-Dan Wan,&nbsp;Shuang-Ling Wu,&nbsp;Jia-Yan Liu,&nbsp;Dong-Sheng Chen","doi":"10.1002/jhet.4883","DOIUrl":"10.1002/jhet.4883","url":null,"abstract":"<div>\u0000 \u0000 <p>A one-pot, three-component reaction of ethyl 5-aminobenzofuran-2-carboxylate, arylglyoxals and cyclic 1,3-dicarbonyl compounds in the presence of acetic acid as an organocatalyst in ethanol medium under reflux conditions provided a series of new 6<i>H</i>-furo[3,2-<i>e</i>]indole derivatives in good yields.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1613-1621"},"PeriodicalIF":2.0,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142209404","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 Oxaazaisowurtzitane Derivatives Via Condensation of p-Toluenesulfonamide With Glyoxal 通过对甲苯磺酰胺与乙二醛缩合合成噁唑烷-乌齐坦衍生物
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-08-27 DOI: 10.1002/jhet.4885
Artyom E. Paromov, Valentina А. Kubasova, Sergey V. Sysolyatin
{"title":"Synthesis of Oxaazaisowurtzitane Derivatives Via Condensation of p-Toluenesulfonamide With Glyoxal","authors":"Artyom E. Paromov,&nbsp;Valentina А. Kubasova,&nbsp;Sergey V. Sysolyatin","doi":"10.1002/jhet.4885","DOIUrl":"10.1002/jhet.4885","url":null,"abstract":"<div>\u0000 \u0000 <p>This work presents the study results on the acid-catalyzed cascade condensation of <i>p</i>-toluenesulfonamide with glyoxal in H<sub>2</sub>SO<sub>4</sub> in order to synthesize aza- and oxaazaisowurtzitanes—a platform for promising high-energy-density compounds—and explore their formation processes. The effects of the ratio of starting reactants, acidity, reaction medium concentration, and temperature on this process were studied in detail. Five novel compounds were derived, including four oxaazaisowurtzitanes comprising one to three aza groups, and one condensation intermediate. The most favorable conditions for the formation of the resultant caged compounds were established and some new regularities of the process were revealed. For instance, the reaction medium concentration was discovered for the first time to influence the generation process of oxaazaisowurtzitanes via direct condensation. The limiting stage of the cage formation process of oxaazaisowurtzitanes was identified. The formation rate of the oxaazaisowurtzitanes was shown to be dependent on their structure. The factor dramatically reducing the yield of the oxaazaisowurtzitanes at elevated synthesis temperature was also revealed.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1602-1612"},"PeriodicalIF":2.0,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142209456","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
A regiospecific fischer indole reaction with 3-oxo-24-nor-allobetulin 3-oxo-24-nor-allobetulin 与费舍尔吲哚的区域特异性反应
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-08-04 DOI: 10.1002/jhet.4877
Liana Zakirova, Irina Baikova, Alexander Lobov, Yury Gatilov, Dmitriy Polovyanenko, Oxana Каzakova
{"title":"A regiospecific fischer indole reaction with 3-oxo-24-nor-allobetulin","authors":"Liana Zakirova,&nbsp;Irina Baikova,&nbsp;Alexander Lobov,&nbsp;Yury Gatilov,&nbsp;Dmitriy Polovyanenko,&nbsp;Oxana Каzakova","doi":"10.1002/jhet.4877","DOIUrl":"10.1002/jhet.4877","url":null,"abstract":"<p>First case of regiospecific formation of indole fused with a triterpene scaffold is observed. Starting from 3-oxo-24-nor-allobetulin Fischer reaction with phenylhydrazine under the influence of weak acid catalyst led to 3H-indole (indolenine) 4. This process was accompanied by a change in the configuration of the methyl group at C-4 that was confirmed by x-ray diffraction method. On the other hand, 3,2-indole 5 was synthesized under the influence of strong acid catalyst (using phenylhydrazine hydrochloride in AcOH acid or phenylhydrazine in MeOH with a few drops of HCl).</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1597-1601"},"PeriodicalIF":2.0,"publicationDate":"2024-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141937851","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
An efficient one-pot, three-component synthesis of novel [1,2,4]triazolo [4′,3′:1,5][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives and their molecular docking studies 新型[1,2,4]三唑并[4′,3′:1,5][1,2,4]三唑并[3,4-b][1,3,4]噻二嗪衍生物的高效一锅三组分合成及其分子对接研究
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-07-30 DOI: 10.1002/jhet.4873
Parameshwara Chary Jilloju, Perugu Shyam, Seema Aravind, Rajeswar Rao Vedula
{"title":"An efficient one-pot, three-component synthesis of novel [1,2,4]triazolo [4′,3′:1,5][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives and their molecular docking studies","authors":"Parameshwara Chary Jilloju,&nbsp;Perugu Shyam,&nbsp;Seema Aravind,&nbsp;Rajeswar Rao Vedula","doi":"10.1002/jhet.4873","DOIUrl":"10.1002/jhet.4873","url":null,"abstract":"<p>A series of novel [1,2,4]triazolo[4′,3′:1,5][1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (<b>4a-p</b>) were synthesized from the reaction of 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol (<b>1</b>) with different bromoethanones (<b>2a-p</b>) and substituted benzoic acids (<b>3</b>) via a one-pot, three-component reaction with good to excellent yields. The new fused tri-cyclic system was achieved without using a catalyst and metal by cyclo-condensation reaction through a one-pot approach. The structures of newly synthesized molecules were confirmed by using IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, Mass spectral, and analytical data. Molecular docking studies were carried out for the newly synthesized compounds against human cancer receptors (2TKB) with good results.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1586-1596"},"PeriodicalIF":2.0,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141870256","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
An approach for the diastereoselective synthesis of (R)-(+)-methyl pipecolate and (+)-dextro-erythrophacetoperane from (S)-(−)-methylbenzylamine 从(S)-(-)-甲基苄胺非对映选择性合成(R)-(+)-甲基哌啶酮和(+)-右旋赤式乙酰哌啶的方法
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-07-23 DOI: 10.1002/jhet.4878
Alan Aguilar-Aguilar, Alan Carrasco-Carballo, Dino Gnecco, Hisami Rodríguez-Matsui, David Aparicio-Solano, Joel L. Terán
{"title":"An approach for the diastereoselective synthesis of (R)-(+)-methyl pipecolate and (+)-dextro-erythrophacetoperane from (S)-(−)-methylbenzylamine","authors":"Alan Aguilar-Aguilar,&nbsp;Alan Carrasco-Carballo,&nbsp;Dino Gnecco,&nbsp;Hisami Rodríguez-Matsui,&nbsp;David Aparicio-Solano,&nbsp;Joel L. Terán","doi":"10.1002/jhet.4878","DOIUrl":"10.1002/jhet.4878","url":null,"abstract":"<p>A diastereoselective synthesis for the preparation of (<i>R</i>)-methyl pipecolate and dextro-erythrophacetoperane, analogs of methylphenidate, drugs used to treat attention deficit hyperactivity disorder, is reported. The key steps involve a high diastereoselective ring-closing reaction via enolate formation and a diastereoselective ketone reduction reaction. The total synthesis of these valuable drugs could be obtained in only 5 and 8 steps, respectively, starting from (<i>S</i>)-(−)-methyl benzylamine.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1571-1579"},"PeriodicalIF":2.0,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141776931","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
A novel and convenient method for the synthesis of 1,2,4-oxadiazole-5-thiones 合成 1,2,4-噁二唑-5-硫酮的新颖简便方法
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-07-23 DOI: 10.1002/jhet.4874
Babak Kaboudin, Saman Soleymanie, Ali Sabzalipour, Foad Kazemi, Haruhiko Fukaya
{"title":"A novel and convenient method for the synthesis of 1,2,4-oxadiazole-5-thiones","authors":"Babak Kaboudin,&nbsp;Saman Soleymanie,&nbsp;Ali Sabzalipour,&nbsp;Foad Kazemi,&nbsp;Haruhiko Fukaya","doi":"10.1002/jhet.4874","DOIUrl":"10.1002/jhet.4874","url":null,"abstract":"<p>A novel and convenient method for the synthesis of 1,2,4-oxadiazole-5-thiones with carbon disulfide as effective C=S source has been developed in a super basic condition. The presented method has a broad substrate scope, and various corresponding 1,2,4-oxadiazole-5-thiones have been obtained in good to excellent yields. This method allows to the gram-scale synthesis of products. Under similar conditions, synthesis of diazole thione benzothioamide derivative from <i>p-</i>cyanobenzamidoxime with CS<sub>2</sub> has been successfully achieved.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1564-1570"},"PeriodicalIF":2.0,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141785668","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
Potential synthesis of nitrated products from 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane derivatives with linear substituents 从具有线性取代基的 2,6,8,12-四乙酰基-2,4,6,8,10,12-六氮杂昭乌齐坦衍生物合成硝化产品的可能性
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-07-23 DOI: 10.1002/jhet.4879
Daria A. Kulagina, Sergey V. Sysolyatin, Yuri A. Balakhnin, Valeria V. Eremina, Natalia A. Alekseeva
{"title":"Potential synthesis of nitrated products from 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane derivatives with linear substituents","authors":"Daria A. Kulagina,&nbsp;Sergey V. Sysolyatin,&nbsp;Yuri A. Balakhnin,&nbsp;Valeria V. Eremina,&nbsp;Natalia A. Alekseeva","doi":"10.1002/jhet.4879","DOIUrl":"10.1002/jhet.4879","url":null,"abstract":"<p>The compact, nitrogen-rich structure of 2,4,6,8,10,12-hexaazaisowurtzitanes calls attention among researchers worldwide. These compounds have found the greatest utility as substrates for nitration to obtain the caged polynitramine, 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, which possesses a high-energy performance. All new derivatives of hexaazaisowurtzitane are nitratable. The present study examined the nitration process of 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane derivatives obtained through the condensation reaction with aldehydes under various conditions to yield CL-20. The yield of CL-20, a well-known nitration product of hexaazaisowurtzitane compounds, was found to depend on the substrate structure and the nitrating mixture composition. The revealed dependence of the synthesis of various nitrated compounds on the holding time enables the synthesis of products with different physicochemical properties in a single process.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1580-1585"},"PeriodicalIF":2.0,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141776932","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 substituted 5,6,7,8-tetrafluoro-1H-benzo[f]indol-4,9-diones based on the reaction of hexafluoro-1,4-napthoquinone with methyl 3-aminocrotonates 基于六氟-1,4-萘醌与 3-氨基巴豆酸甲酯反应合成取代的 5,6,7,8-四氟-1H-苯并[f]吲哚-4,9-二酮
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-07-23 DOI: 10.1002/jhet.4872
Ekaterina N. Kudryavtseva, Boris V. Lichitsky, Andrey N. Komogortsev, Constantine V. Milyutin, Evgeny V. Tretyakov
{"title":"Synthesis of substituted 5,6,7,8-tetrafluoro-1H-benzo[f]indol-4,9-diones based on the reaction of hexafluoro-1,4-napthoquinone with methyl 3-aminocrotonates","authors":"Ekaterina N. Kudryavtseva,&nbsp;Boris V. Lichitsky,&nbsp;Andrey N. Komogortsev,&nbsp;Constantine V. Milyutin,&nbsp;Evgeny V. Tretyakov","doi":"10.1002/jhet.4872","DOIUrl":"10.1002/jhet.4872","url":null,"abstract":"<p>For the first time, the possibility of using hexafluoro-1,4-naphthoquinone for the construction of condensed heterocyclic system was demonstrated. As a result, two-step synthesis of previously unknown 5,6,7,8-tetrafluoro-1<i>H</i>-benzo[<i>f</i>]indol-4,9-dione derivatives was elaborated. The suggested method includes initial interaction of hexafluoro-1,4-naphthoquinone with various methyl 3-aminocrotonates and subsequent intramolecular cyclization into the target fluorinated benzo[<i>f</i>]indole-4,9-diones. The distinctive feature of considered protocol is regiospecific reaction of fluorine atoms in quinone fragment. Advantages of the presented approach are simple synthetic procedure avoiding chromatographic purification, atom economy and readily available starting materials. The structure of one of the synthesized compounds was established by x-ray analysis.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1554-1563"},"PeriodicalIF":2.0,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141776989","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
Design, synthesis, biological evaluation of a new tricyclicthiazolopy-rimidinone derivatives as acetylcholinesterase inhibitors 作为乙酰胆碱酯酶抑制剂的新型三环噻唑并嘧啶酮衍生物的设计、合成和生物学评价
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-07-19 DOI: 10.1002/jhet.4863
Yan Zeng, Lifei Nie, Liu Liu, Khurshed Bozorov, Jiangyu Zhao
{"title":"Design, synthesis, biological evaluation of a new tricyclicthiazolopy-rimidinone derivatives as acetylcholinesterase inhibitors","authors":"Yan Zeng,&nbsp;Lifei Nie,&nbsp;Liu Liu,&nbsp;Khurshed Bozorov,&nbsp;Jiangyu Zhao","doi":"10.1002/jhet.4863","DOIUrl":"10.1002/jhet.4863","url":null,"abstract":"<p>The novel serious of tricyclicthiazolo[5,4-<i>d</i>]pyrimidinone were designed and synthesized as acetylcholinesterase (AChE) inhibitor agents. The main factors affecting the reactions of syntheses and the structure–activity relationships (SARs) were investigated as well. All compounds were confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The in vitro enzyme assays proved that most of the compounds effectively inhibited AChE in the micromolar range with little cytotoxicity. Especially the compound <b>G15</b> exhibited the best inhibitory activity against AChE with IC<sub>50</sub> values of 4.41 ± 0.46 μM. Furthermore, kinetic analysis and molecular modeling studies pointed out the competitive inhibition manner of <b>G15</b> on AChE. Thus, the derivative <b>G15</b> can be considered a promising leading compound on AChE.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1542-1553"},"PeriodicalIF":2.0,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141740493","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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