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A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis.

The Journal of organic chemistry

Bunrit A, Sawadjoon S, Tšupova S, Sjöberg PJ, Samec JS.
PMID: 26789020
J Org Chem. 2016 Feb 19;81(4):1450-60. doi: 10.1021/acs.joc.5b02581. Epub 2016 Feb 04.

An atom-efficient route to pyrroles substituted in the β-position has been achieved in four high yielding steps by a combination of Pd, Ru, and Fe catalysis with only water and ethene as side-products. The reaction is general and gives...

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Bunrit A, Sawadjoon S, Tšupova S, et al. A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis. J Org Chem. 2016;81(4):1450-60doi: 10.1021/acs.joc.5b02581.
Bunrit, A., Sawadjoon, S., Tšupova, S., Sjöberg, P. J., & Samec, J. S. (2016). A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis. The Journal of organic chemistry, 81(4), 1450-60. https://doi.org/10.1021/acs.joc.5b02581
Bunrit, Anon, et al. "A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis." The Journal of organic chemistry vol. 81,4 (2016): 1450-60. doi: https://doi.org/10.1021/acs.joc.5b02581
Bunrit A, Sawadjoon S, Tšupova S, Sjöberg PJ, Samec JS. A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis. J Org Chem. 2016 Feb 19;81(4):1450-60. doi: 10.1021/acs.joc.5b02581. Epub 2016 Feb 04. PMID: 26789020.
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Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions.

Chemical Society reviews

Kim DS, Sessler JL.
PMID: 24984014
Chem Soc Rev. 2015 Jan 21;44(2):532-46. doi: 10.1039/c4cs00157e.

Over the last two decades, calix[4]pyrroles have attracted considerable attention as molecular containers. Used in this capacity, they have been exploited as strong and selective receptors and as extractants for both anions and ion pairs. More recently, calix[4]pyrroles have...

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Kim DS, Sessler JL. Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions. Chem Soc Rev. 2015;44(2):532-46doi: 10.1039/c4cs00157e.
Kim, D. S., & Sessler, J. L. (2015). Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions. Chemical Society reviews, 44(2), 532-46. https://doi.org/10.1039/c4cs00157e
Kim, Dong Sub, and Sessler, Jonathan L. "Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions." Chemical Society reviews vol. 44,2 (2015): 532-46. doi: https://doi.org/10.1039/c4cs00157e
Kim DS, Sessler JL. Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions. Chem Soc Rev. 2015 Jan 21;44(2):532-46. doi: 10.1039/c4cs00157e. PMID: 24984014.
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Multicomponent one-pot synthesis of highly-functionalized pyrrole-3-carbonitriles in aqueous medium and their computational study.

Organic & biomolecular chemistry

Pagadala R, Kommidi DR, Kankala S, Maddila S, Singh P, Moodley B, Koorbanally NA, Jonnalagadda SB.
PMID: 25503439
Org Biomol Chem. 2015 Feb 14;13(6):1800-6. doi: 10.1039/c4ob02229g.

A one-pot green protocol involving four-components in aqueous medium is developed to synthesize highly-functionalized pyrroles in good yields. Two of the newly synthesized compounds were subjected to in silico analysis on the Pharm Mapper web-server and the human mitogen-activated...

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Pagadala R, Kommidi DR, Kankala S, et al. Multicomponent one-pot synthesis of highly-functionalized pyrrole-3-carbonitriles in aqueous medium and their computational study. Org Biomol Chem. 2015;13(6):1800-6doi: 10.1039/c4ob02229g.
Pagadala, R., Kommidi, D. R., Kankala, S., Maddila, S., Singh, P., Moodley, B., Koorbanally, N. A., & Jonnalagadda, S. B. (2015). Multicomponent one-pot synthesis of highly-functionalized pyrrole-3-carbonitriles in aqueous medium and their computational study. Organic & biomolecular chemistry, 13(6), 1800-6. https://doi.org/10.1039/c4ob02229g
Pagadala, Ramakanth, et al. "Multicomponent one-pot synthesis of highly-functionalized pyrrole-3-carbonitriles in aqueous medium and their computational study." Organic & biomolecular chemistry vol. 13,6 (2015): 1800-6. doi: https://doi.org/10.1039/c4ob02229g
Pagadala R, Kommidi DR, Kankala S, Maddila S, Singh P, Moodley B, Koorbanally NA, Jonnalagadda SB. Multicomponent one-pot synthesis of highly-functionalized pyrrole-3-carbonitriles in aqueous medium and their computational study. Org Biomol Chem. 2015 Feb 14;13(6):1800-6. doi: 10.1039/c4ob02229g. PMID: 25503439.
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A mild and efficient AgSbF.

Tetrahedron

Gujarathi S, Liu X, Song L, Hendrickson H, Zheng G.
PMID: 25061238
Tetrahedron. 2014 Aug 26;70(34):5267-5273. doi: 10.1016/j.tet.2014.05.073.

Development of an efficient synthesis of fully substituted pyrroles via a sequential as a catalyst. The propargylation/amination/cycloisomerization was accomplished using AgSbF

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Gujarathi S, Liu X, Song L, et al. A mild and efficient AgSbF. Tetrahedron. 2014;70(34):5267-5273doi: 10.1016/j.tet.2014.05.073.
Gujarathi, S., Liu, X., Song, L., Hendrickson, H., & Zheng, G. (2014). A mild and efficient AgSbF. Tetrahedron, 70(34), 5267-5273. https://doi.org/10.1016/j.tet.2014.05.073
Gujarathi, Satheesh, et al. "A mild and efficient AgSbF." Tetrahedron vol. 70,34 (2014): 5267-5273. doi: https://doi.org/10.1016/j.tet.2014.05.073
Gujarathi S, Liu X, Song L, Hendrickson H, Zheng G. A mild and efficient AgSbF. Tetrahedron. 2014 Aug 26;70(34):5267-5273. doi: 10.1016/j.tet.2014.05.073. PMID: 25061238; PMCID: PMC4104368.
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Dimethyl sulfoxide participant iron-mediated cascade oxidation/α-formylation reaction of substituted 2,3-dihydropyrroles under air and protonic acid free condition.

The Journal of organic chemistry

Zhang Z, Tian Q, Qian J, Liu Q, Liu T, Shi L, Zhang G.
PMID: 25088721
J Org Chem. 2014 Sep 05;79(17):8182-8. doi: 10.1021/jo501385w. Epub 2014 Aug 18.

An efficient and Brønsted acid free one-pot protocol to directly generate structurally sophisticated α-formylpyrrole derivatives in moderate to good yields has been demonstrated, involving an iron-mediated domino oxidation/formylation reaction of readily available 2,3-dihydro-1H-pyrroles in dimethyl sulfoxide and air atmosphere,...

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Zhang Z, Tian Q, Qian J, et al. Dimethyl sulfoxide participant iron-mediated cascade oxidation/α-formylation reaction of substituted 2,3-dihydropyrroles under air and protonic acid free condition. J Org Chem. 2014;79(17):8182-8doi: 10.1021/jo501385w.
Zhang, Z., Tian, Q., Qian, J., Liu, Q., Liu, T., Shi, L., & Zhang, G. (2014). Dimethyl sulfoxide participant iron-mediated cascade oxidation/α-formylation reaction of substituted 2,3-dihydropyrroles under air and protonic acid free condition. The Journal of organic chemistry, 79(17), 8182-8. https://doi.org/10.1021/jo501385w
Zhang, Zhiguo, et al. "Dimethyl sulfoxide participant iron-mediated cascade oxidation/α-formylation reaction of substituted 2,3-dihydropyrroles under air and protonic acid free condition." The Journal of organic chemistry vol. 79,17 (2014): 8182-8. doi: https://doi.org/10.1021/jo501385w
Zhang Z, Tian Q, Qian J, Liu Q, Liu T, Shi L, Zhang G. Dimethyl sulfoxide participant iron-mediated cascade oxidation/α-formylation reaction of substituted 2,3-dihydropyrroles under air and protonic acid free condition. J Org Chem. 2014 Sep 05;79(17):8182-8. doi: 10.1021/jo501385w. Epub 2014 Aug 18. PMID: 25088721.
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BORON CATALYSIS. Metal-free catalytic C-H bond activation and borylation of heteroarenes.

Science (New York, N.Y.)

Légaré MA, Courtemanche MA, Rochette É, Fontaine FG.
PMID: 26228143
Science. 2015 Jul 31;349(6247):513-6. doi: 10.1126/science.aab3591.

Transition metal complexes are efficient catalysts for the C-H bond functionalization of heteroarenes to generate useful products for the pharmaceutical and agricultural industries. However, the costly need to remove potentially toxic trace metals from the end products has prompted...

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Légaré MA, Courtemanche MA, Rochette É, et al. BORON CATALYSIS. Metal-free catalytic C-H bond activation and borylation of heteroarenes. Science. 2015;349(6247):513-6doi: 10.1126/science.aab3591.
Légaré, M. A., Courtemanche, M. A., Rochette, �. �., & Fontaine, F. G. (2015). BORON CATALYSIS. Metal-free catalytic C-H bond activation and borylation of heteroarenes. Science (New York, N.Y.), 349(6247), 513-6. https://doi.org/10.1126/science.aab3591
Légaré, Marc-André, et al. "BORON CATALYSIS. Metal-free catalytic C-H bond activation and borylation of heteroarenes." Science (New York, N.Y.) vol. 349,6247 (2015): 513-6. doi: https://doi.org/10.1126/science.aab3591
Légaré MA, Courtemanche MA, Rochette É, Fontaine FG. BORON CATALYSIS. Metal-free catalytic C-H bond activation and borylation of heteroarenes. Science. 2015 Jul 31;349(6247):513-6. doi: 10.1126/science.aab3591. PMID: 26228143.
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Cascade Reactions in Quantitative Solid-State Syntheses.

Angewandte Chemie (International ed. in English)

Kaupp G, Schmeyers J, Kuse A, Atfeh A.
PMID: 10540385
Angew Chem Int Ed Engl. 1999 Oct 04;38(19):2896-2899.

100 % yield in the absence of the liquid phase: A one-pot synthesis of highly substituted pyrroles, which proceeds in solution with moderate yields, functions quantitatively in the solid-solid variant, and that at much lower temperatures, although at least...

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Kaupp G, Schmeyers J, Kuse A, et al. Cascade Reactions in Quantitative Solid-State Syntheses. Angew Chem Int Ed Engl. 1999;38(19):2896-2899
Kaupp, G., Schmeyers, J., Kuse, A., & Atfeh, A. (1999). Cascade Reactions in Quantitative Solid-State Syntheses. Angewandte Chemie (International ed. in English), 38(19), 2896-2899.
Kaupp, et al. "Cascade Reactions in Quantitative Solid-State Syntheses." Angewandte Chemie (International ed. in English) vol. 38,19 (1999): 2896-2899.
Kaupp G, Schmeyers J, Kuse A, Atfeh A. Cascade Reactions in Quantitative Solid-State Syntheses. Angew Chem Int Ed Engl. 1999 Oct 04;38(19):2896-2899. PMID: 10540385.
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A one-step synthesis of fused pentathiepins.

Chemical communications (Cambridge, England)

Konstantinova LS, Rakitin OA, Rees CW.
PMID: 12109083
Chem Commun (Camb). 2002 Jun 07;(11):1204-5. doi: 10.1039/b203349f.

Treatment of nucleophilic heterocycles like pyrroles and thiophene, and their tetrahydro derivatives, with S2Cl2 and a base in chloroform at room temperature provides a simple one-pot synthesis of heterocyclic fused mono and bis pentathiepins such as 2, 3, 4,...

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Konstantinova LS, Rakitin OA, Rees CW. A one-step synthesis of fused pentathiepins. Chem Commun (Camb). 2002;(11):1204-5doi: 10.1039/b203349f.
Konstantinova, L. S., Rakitin, O. A., & Rees, C. W. (2002). A one-step synthesis of fused pentathiepins. Chemical communications (Cambridge, England), (11), 1204-5. https://doi.org/10.1039/b203349f
Konstantinova, Lidia S, et al. "A one-step synthesis of fused pentathiepins." Chemical communications (Cambridge, England) vol. ,11 (2002): 1204-5. doi: https://doi.org/10.1039/b203349f
Konstantinova LS, Rakitin OA, Rees CW. A one-step synthesis of fused pentathiepins. Chem Commun (Camb). 2002 Jun 07;(11):1204-5. doi: 10.1039/b203349f. PMID: 12109083.
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1,4-Disubstituted and 1,4,5-Trisubstituted 2-[(Benzotriazol-1-yl)methyl]pyrroles as Versatile Synthetic Intermediates.

The Journal of organic chemistry

Katritzky AR, Li J.
PMID: 11667027
J Org Chem. 1996 Mar 08;61(5):1624-1628. doi: 10.1021/jo951894m.

The CH(2)Bt substituent, unlike previously used CH(2)X substituents, enables (i) the synthetic elaboration of pyrroles with unsubstituted ring positions and (ii) electrophilic as well as nucleophilic substitutions to give pyrroles of type pyrrolyl-2-CHENu. Thus, 1,4-disubstituted (7) and 1,4,5-trisubstituted 2-[(benzotriazol-1-yl)methyl]pyrroles...

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Katritzky AR, Li J. 1,4-Disubstituted and 1,4,5-Trisubstituted 2-[(Benzotriazol-1-yl)methyl]pyrroles as Versatile Synthetic Intermediates. J Org Chem. 1996;61(5):1624-1628doi: 10.1021/jo951894m.
Katritzky, A. R., & Li, J. (1996). 1,4-Disubstituted and 1,4,5-Trisubstituted 2-[(Benzotriazol-1-yl)methyl]pyrroles as Versatile Synthetic Intermediates. The Journal of organic chemistry, 61(5), 1624-1628. https://doi.org/10.1021/jo951894m
Katritzky, Alan R., and Li, Jianqing. "1,4-Disubstituted and 1,4,5-Trisubstituted 2-[(Benzotriazol-1-yl)methyl]pyrroles as Versatile Synthetic Intermediates." The Journal of organic chemistry vol. 61,5 (1996): 1624-1628. doi: https://doi.org/10.1021/jo951894m
Katritzky AR, Li J. 1,4-Disubstituted and 1,4,5-Trisubstituted 2-[(Benzotriazol-1-yl)methyl]pyrroles as Versatile Synthetic Intermediates. J Org Chem. 1996 Mar 08;61(5):1624-1628. doi: 10.1021/jo951894m. PMID: 11667027.
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Photochemical transformations of 2,2'-(1,2-phenylenedivinylene)-dipyrroles.

Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

Basarić N, Marinić Z, Visnjevac A, Kojić-Prodić B, Griesbeck AG, Sindler-Kulyk M.
PMID: 12661601
Photochem Photobiol Sci. 2002 Dec;1(12):1017-23. doi: 10.1039/b209127e.

The photochemistry of 2,2'-(1,2-phenylenedivinylene)dipyrroles (4a,b) has been investigated under various conditions. After excitation of the starting material, an electron transfer followed by hydrogen transfer and radical combination occurs giving 2-[[1-(2H-pyrrol-2-ylidene)methinyl]-2-indanyl]pyrrole (14) as the intermediate. The intermediate could not be...

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Basarić N, Marinić Z, Visnjevac A, et al. Photochemical transformations of 2,2'-(1,2-phenylenedivinylene)-dipyrroles. Photochem Photobiol Sci. 2002;1(12):1017-23doi: 10.1039/b209127e.
Basarić, N., Marinić, Z., Visnjevac, A., Kojić-Prodić, B., Griesbeck, A. G., & Sindler-Kulyk, M. (2002). Photochemical transformations of 2,2'-(1,2-phenylenedivinylene)-dipyrroles. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 1(12), 1017-23. https://doi.org/10.1039/b209127e
Basarić, Nikola, et al. "Photochemical transformations of 2,2'-(1,2-phenylenedivinylene)-dipyrroles." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 1,12 (2002): 1017-23. doi: https://doi.org/10.1039/b209127e
Basarić N, Marinić Z, Visnjevac A, Kojić-Prodić B, Griesbeck AG, Sindler-Kulyk M. Photochemical transformations of 2,2'-(1,2-phenylenedivinylene)-dipyrroles. Photochem Photobiol Sci. 2002 Dec;1(12):1017-23. doi: 10.1039/b209127e. PMID: 12661601.
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Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions.

The Journal of organic chemistry

Aelterman W, De Kimpe N, Tyvorskii V, Kulinkovich O.
PMID: 11429929
J Org Chem. 2001 Jan 12;66(1):53-8. doi: 10.1021/jo000724t.

A new synthesis of 2,3-disubstituted pyrroles and pyridines is described. The reaction of 3-halo-1-azaallylic carbanions, regiospecifically generated from alpha-halogenated ketimines, with omega-iodoazides led to the regiospecific formation of omega-azido-alpha-haloketimines. Treatment of these functionalized imines with tin(II) chloride afforded halogenated...

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Aelterman W, De Kimpe N, Tyvorskii V, et al. Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions. J Org Chem. 2001;66(1):53-8doi: 10.1021/jo000724t.
Aelterman, W., De Kimpe, N., Tyvorskii, V., & Kulinkovich, O. (2001). Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions. The Journal of organic chemistry, 66(1), 53-8. https://doi.org/10.1021/jo000724t
Aelterman, W, et al. "Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions." The Journal of organic chemistry vol. 66,1 (2001): 53-8. doi: https://doi.org/10.1021/jo000724t
Aelterman W, De Kimpe N, Tyvorskii V, Kulinkovich O. Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions. J Org Chem. 2001 Jan 12;66(1):53-8. doi: 10.1021/jo000724t. PMID: 11429929.
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Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles.

The Journal of organic chemistry

García Ruano JL, Tito A, Peromingo MT.
PMID: 11856048
J Org Chem. 2002 Feb 08;67(3):981-7. doi: 10.1021/jo010797s.

The first 1,3-dipolar reaction of azomethine ylides with optically pure vinyl sulfoxide are reported. The presence of the sulfinyl group increase the reactivity of the acrylate moiety as a dipolarophile, and the reactions evolve with complete regio- and endo-selectivities....

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García Ruano JL, Tito A, Peromingo MT. Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles. J Org Chem. 2002;67(3):981-7doi: 10.1021/jo010797s.
García Ruano, J. L., Tito, A., & Peromingo, M. T. (2002). Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles. The Journal of organic chemistry, 67(3), 981-7. https://doi.org/10.1021/jo010797s
García Ruano, José Luis, et al. "Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles." The Journal of organic chemistry vol. 67,3 (2002): 981-7. doi: https://doi.org/10.1021/jo010797s
García Ruano JL, Tito A, Peromingo MT. Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles. J Org Chem. 2002 Feb 08;67(3):981-7. doi: 10.1021/jo010797s. PMID: 11856048.
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Showing 25 to 36 of 862 entries