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.
{"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}
Chul-bae Kim, C. Cho, Chang Keun Kim, Kwangyong Park
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.
{"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}
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...
{"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}
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.
{"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}
Gang Liu, Li Li, Binbin Kou, Suode Zhang, Liang Zhang, Yunyun Yuan, Tao Ma, Yan Shang, Yuancheng Li
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.
{"title":"Benzofused tricycles based on 2-quinoxalinol.","authors":"Gang Liu, Li Li, Binbin Kou, Suode Zhang, Liang Zhang, Yunyun Yuan, Tao Ma, Yan Shang, 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}
Zhibo Ma, Zheng Xiang, T. Luo, K. Lu, Zhibin Xu, Jia-Hua Chen, Zhen Yang
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.
{"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}
Johan S Paul, R. Janssens, J. Denayer, G. Baron, P. Jacobs
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.
{"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}
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.
{"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}
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