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Journal of combinatorial chemistry最新文献

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Fluorous and traceless synthesis of substituted indole alkaloids. 含氟和无迹取代吲哚生物碱的合成。
Journal of combinatorial chemistry Pub Date : 2007-10-04 DOI: 10.1002/CHIN.200814216
Mei-Jung Lin, Wei Zhang, Chung‐Ming Sun
{"title":"Fluorous and traceless synthesis of substituted indole alkaloids.","authors":"Mei-Jung Lin, Wei Zhang, Chung‐Ming Sun","doi":"10.1002/CHIN.200814216","DOIUrl":"https://doi.org/10.1002/CHIN.200814216","url":null,"abstract":"The fluorous traceless synthesis of substituted indole alkaloids is carried out first by attaching the 3-(perfluorooctyl)propanol with Boc protected L-tryptophan. The reaction of perfluoroalkyl (Rfh)-tagged tryptophan esters with various aldehydes undergoes Pictet-Spengler reaction to give cis and trans stereoisomers of tetrahydro-beta-carbolines. The nucleophilic addition of the piperidine nitrogen across various isocyanates is followed by the cyclization of ureas and simultaneous rupture of the fluorous tag to afford the hydantoin ring fused tetrahydro-beta-carbolines. All the fluorous-tag compounds are purified by solid-phase extraction (SPE) through Fluoro Flash cartridges.","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"55 1","pages":"951-8"},"PeriodicalIF":0.0,"publicationDate":"2007-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200814216","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51055289","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 9
Traceless liquid-phase synthesis of biphenyls and terphenyls using pentaerythritol as a tetrapodal soluble support. 以季戊四醇为四足可溶性载体的无迹液相合成联苯和三苯。
Journal of combinatorial chemistry Pub Date : 2007-09-28 DOI: 10.1002/CHIN.200814099
Chul-bae Kim, C. Cho, Chang Keun Kim, Kwangyong Park
{"title":"Traceless liquid-phase synthesis of biphenyls and terphenyls using pentaerythritol as a tetrapodal soluble support.","authors":"Chul-bae Kim, C. Cho, Chang Keun Kim, Kwangyong Park","doi":"10.1002/CHIN.200814099","DOIUrl":"https://doi.org/10.1002/CHIN.200814099","url":null,"abstract":"Application of a novel sulfonate-based traceless multifunctional linker system using pentaerythritol as a tetrapodal soluble support was demonstrated using liquid-phase parallel and combinatorial preparation of biphenyl and terphenyl compounds. Nickel-catalyzed reactions of pentaerythritol tetrakis(arenesulfonate)s with arylmagnesium bromides generated the desired products in sufficient yields through reductive cleavage/cross-coupling of the C-S bond. Homogeneous pentaerythritol-supported reactions could be accomplished using less nucleophile with shorter reaction periods than could the corresponding heterogeneous polymer-supported reactions. This liquid-phase approach using a small polyfunctionalized support combines advantages of solution-phase and solid-phase syntheses by allowing high reactivity, high atom economy, simple isolation, and real-time monitoring of the reaction progress.","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"9 6 1","pages":"1157-63"},"PeriodicalIF":0.0,"publicationDate":"2007-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200814099","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51054850","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 12
Microwave-enhanced one-pot synthesis of diversified 3-acyl-5-hydroxybenzofurans. 微波强化一锅法合成多种3-酰基-5-羟基苯并呋喃。
Journal of combinatorial chemistry Pub Date : 2007-08-31 DOI: 10.1002/CHIN.200814120
Xia-Min Cheng, Xue‐Wei Liu
{"title":"Microwave-enhanced one-pot synthesis of diversified 3-acyl-5-hydroxybenzofurans.","authors":"Xia-Min Cheng, Xue‐Wei Liu","doi":"10.1002/CHIN.200814120","DOIUrl":"https://doi.org/10.1002/CHIN.200814120","url":null,"abstract":"An efficient one-pot two-step synthesis of diversified 3-acyl-5-hydroxybenzofurans under microwave irradiation is described. The desired products were synthesized rapidly by adopting the Nenitzescu...","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"9 6 1","pages":"906-8"},"PeriodicalIF":0.0,"publicationDate":"2007-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200814120","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51055205","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 34
Diversity-oriented synthesis of functionalized quinolin-2(1H)-ones via Pd-catalyzed site-selective cross-coupling reactions. 利用pd催化的位点选择性交叉偶联反应合成功能化喹啉-2(1H)- 1。
Journal of combinatorial chemistry Pub Date : 2007-08-10 DOI: 10.1002/CHIN.200806132
Zhiyong Wang, Bing Wang, Jie Wu
{"title":"Diversity-oriented synthesis of functionalized quinolin-2(1H)-ones via Pd-catalyzed site-selective cross-coupling reactions.","authors":"Zhiyong Wang, Bing Wang, Jie Wu","doi":"10.1002/CHIN.200806132","DOIUrl":"https://doi.org/10.1002/CHIN.200806132","url":null,"abstract":"Biologically active 3-amino-4-arylquinolin-2(1H)-ones and 3-alkenyl-4-arylquinolin-2(1H)-ones were synthesized in an efficient and concise manner, utilizing readily available 4-hydroxyquinolin-2(1H)-one as starting material. The key steps, which introduced selectivity and diversity in the synthesis, were the palladium-catalyzed site-selective Suzuki-Miyaura/Buchwald-Hartwig amination and Suzuki-Miyaura/Heck coupling reactions of 3-bromo-4-trifloxy-quinolin-2(1H)-one.","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"9 5 1","pages":"811-7"},"PeriodicalIF":0.0,"publicationDate":"2007-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200806132","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51053225","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 38
Benzofused tricycles based on 2-quinoxalinol. 基于2-喹啉醇的苯并杂化三轮车。
Journal of combinatorial chemistry Pub Date : 2007-01-01 DOI: 10.1021/cc060034o
Gang Liu, Li Li, Binbin Kou, Suode Zhang, Liang Zhang, Yunyun Yuan, Tao Ma, Yan Shang, Yuancheng Li
{"title":"Benzofused tricycles based on 2-quinoxalinol.","authors":"Gang Liu,&nbsp;Li Li,&nbsp;Binbin Kou,&nbsp;Suode Zhang,&nbsp;Liang Zhang,&nbsp;Yunyun Yuan,&nbsp;Tao Ma,&nbsp;Yan Shang,&nbsp;Yuancheng Li","doi":"10.1021/cc060034o","DOIUrl":"https://doi.org/10.1021/cc060034o","url":null,"abstract":"<p><p>This paper describes our recent efforts to synthesize novel compound scaffolds integrating 2-quinoxalinol with privileged structures of 1,3-dihydro-benzoimidazol-2-one, 1,3-dihydro-benzoimidazole-2-thione, 3-hydroxy-1H-quinoxalin-2-one, 2H-benzo[1,4]oxazin-3-ol, 2H-benzo[1,4]thiazin-3-ol, and 1,3,4,5-tetrahydro-benzo[1,4]diazepin-2-one, respectively. Eight novel benzofused tricycles and their substituent diversity points were developed. These include pyrazino[2,3-g]quinoxaline-2,8-diol (I), 3-hydroxy-6,8,9,10-tetrahydro-1,4,6,10-tetraaza-cyclohepta[b]naphthalen-7-one (II), 6-hydroxy-4H-1-oxa-4,5,8-triaza-anthracen-3-one (III), 6-hydroxy-4H-1-thia-4,5,8-triaza-anthracen-3-one (IV), 6-hydroxy-1,1-dioxo-1,4-dihydro-2H-1lambda(6)-thia-4,5,8-triaza-anthracen-3-one (V), 6-hydroxy-1,3-dihydro-imidazo[4,5-g]quinoxalin-2-one (VI), 6-hydroxy-1,3-dihydro-imidazo[4,5-g]quinoxaline-2-thione (VII), and 7-hydroxy-1,4-dihydro-pyrazino[2,3-g]quinoxaline-2,3-dione (VIII). This strategy of integrating two benzofused privileged structures into one molecule may provide a greater chance for the discovery of novel lead compounds.</p>","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"9 1","pages":"70-8"},"PeriodicalIF":0.0,"publicationDate":"2007-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1021/cc060034o","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"26475743","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 functionalized quinolines via Ugi and Pd-catalyzed intramolecular arylation reactions. 通过Ugi和pd催化的分子内芳化反应合成功能化喹啉。
Journal of combinatorial chemistry Pub Date : 2006-07-22 DOI: 10.1002/CHIN.200704139
Zhibo Ma, Zheng Xiang, T. Luo, K. Lu, Zhibin Xu, Jia-Hua Chen, Zhen Yang
{"title":"Synthesis of functionalized quinolines via Ugi and Pd-catalyzed intramolecular arylation reactions.","authors":"Zhibo Ma, Zheng Xiang, T. Luo, K. Lu, Zhibin Xu, Jia-Hua Chen, Zhen Yang","doi":"10.1002/CHIN.200704139","DOIUrl":"https://doi.org/10.1002/CHIN.200704139","url":null,"abstract":"Two types of quinoline scaffolds were constructed in a combinatorial format via the Ugi four-component reaction (U-4CR) and Pd-catalyzed intramolecular arylation reaction. The scope of this two-step synthetic sequence was examined from commercially available and synthetically accessible starting materials.","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"8 5 1","pages":"696-704"},"PeriodicalIF":0.0,"publicationDate":"2006-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200704139","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51040927","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 37
Optimization of MoVSb oxide catalyst for partial oxidation of isobutane by combinatorial approaches. 组合法优化异丁烷部分氧化催化剂的研究。
Journal of combinatorial chemistry Pub Date : 2005-04-23 DOI: 10.1002/CHIN.200538028
Johan S Paul, R. Janssens, J. Denayer, G. Baron, P. Jacobs
{"title":"Optimization of MoVSb oxide catalyst for partial oxidation of isobutane by combinatorial approaches.","authors":"Johan S Paul, R. Janssens, J. Denayer, G. Baron, P. Jacobs","doi":"10.1002/CHIN.200538028","DOIUrl":"https://doi.org/10.1002/CHIN.200538028","url":null,"abstract":"Optimization of the Mo-V-Sb mixed-oxide system for the selective oxidation of isobutane to methacrolein by true combinatorial methods primarily is intended to reduce the number of experiments in a broad parameter space. Therefore, an evolutionary approach based on a genetic algorithm has been chosen to screen three generations of 30 catalysts. With the help of automated sol-gel synthesis techniques, a high-throughput continuous flow reactor (16UPCFR), and appropriate software for experimental design, a new catalyst composition with improved performance has been obtained. Finally, the best catalysts were scaled-up to gram quantities and tested in a continuous-flow reactor unit that was equipped with four parallel reactors (4UPCFR). The final catalyst showed a significantly higher selectivity toward methacrolein at the same isobutane conversion, compared to the initial Mo8V2Sb90O(x) catalyst.","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"317 1","pages":"407-13"},"PeriodicalIF":0.0,"publicationDate":"2005-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200538028","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51026464","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 29
N-Terminal peptide aldehydes as electrophiles in combinatorial solid phase synthesis of novel peptide isosteres. n端肽醛在新型肽同位体组合固相合成中的亲电作用。
Journal of combinatorial chemistry Pub Date : 2001-01-01 DOI: 10.1021/cc000058
T. Groth, M. Meldal
{"title":"N-Terminal peptide aldehydes as electrophiles in combinatorial solid phase synthesis of novel peptide isosteres.","authors":"T. Groth, M. Meldal","doi":"10.1021/cc000058","DOIUrl":"https://doi.org/10.1021/cc000058","url":null,"abstract":"N-Terminal peptide aldehydes were synthesized on a solid support and utilized as electrophiles in nucleophilic reactions in order to furnish novel and diverse peptide isosteres. The aldehyde moiety of the peptide was synthesized by coupling a protected aldehyde building block to the peptide and deprotecting it quantitatively in less than 3 min. It was found that protection of the two succeeding amide nitrogens was necessary in order to avoid reaction between the aldehyde and backbone amides. The N-terminal peptide aldehydes were successfully reacted in the following way: (a) reductive amination with a large variety of amines, leading to N-alkyl-gamma-aminobutyric peptide isosteres positioned centrally in the peptide; (b) reductive amination with amino esters, leading to N-terminal 2,5-diketopiperazine peptides; (c) Horner-Wadsworth-Emmons olefination, leading to unsaturated peptide isosteres positioned centrally in the peptide; and (d) Pictet-Spengler condensations, leading to tetrahydro-beta-carbolines either positioned centrally in a peptide or fused with a diketopiperazine ring in the N-terminus of the peptide.","PeriodicalId":15439,"journal":{"name":"Journal of combinatorial chemistry","volume":"3 1 1","pages":"45-63"},"PeriodicalIF":0.0,"publicationDate":"2001-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1021/cc000058","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"57643852","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 5
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