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Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

Chemistry of heterocyclic compounds

Hasty SJ, Demchenko AV.
PMID: 24288416
Chem Heterocycl Compd (N Y). 2012 Apr;48(1). doi: 10.1007/s10593-012-0984-4.

This review discusses the synthesis and application of glycosyl thioimidates in chemical glycosylation and oligosaccharide assembly. Although glycosyl thioimidates include a broad range of compounds, the discussion herein centers on

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Hasty SJ, Demchenko AV. Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis. Chem Heterocycl Compd (N Y). 2012;48(1)doi: 10.1007/s10593-012-0984-4.
Hasty, S. J., & Demchenko, A. V. (2012). Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis. Chemistry of heterocyclic compounds, 48(1), . https://doi.org/10.1007/s10593-012-0984-4
Hasty, S J, and Demchenko, A V. "Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis." Chemistry of heterocyclic compounds vol. 48,1 (2012). doi: https://doi.org/10.1007/s10593-012-0984-4
Hasty SJ, Demchenko AV. Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis. Chem Heterocycl Compd (N Y). 2012 Apr;48(1). doi: 10.1007/s10593-012-0984-4. PMID: 24288416; PMCID: PMC3840805.
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Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic Alkylation Reaction of MBH Carbonates: Efficient Construction of Seven-Membered Heterocycles.

Organic letters

Chen J, Huang Y.
PMID: 28968108
Org Lett. 2017 Oct 20;19(20):5609-5612. doi: 10.1021/acs.orglett.7b02742. Epub 2017 Oct 02.

Phosphine-catalyzed intermolecular sequential [4 + 3] domino annulation/allylic alkylation of MBH carbonates and N-tosyl azadienes is reported. A series of functionalized benzofuran-fused seven-membered nitrogen-heterocyclic compounds with one quaternary center were obtained in good to excellent yields. In this sequential...

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Chen J, Huang Y. Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic Alkylation Reaction of MBH Carbonates: Efficient Construction of Seven-Membered Heterocycles. Org Lett. 2017;19(20):5609-5612doi: 10.1021/acs.orglett.7b02742.
Chen, J., & Huang, Y. (2017). Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic Alkylation Reaction of MBH Carbonates: Efficient Construction of Seven-Membered Heterocycles. Organic letters, 19(20), 5609-5612. https://doi.org/10.1021/acs.orglett.7b02742
Chen, Junlong, and Huang, You. "Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic Alkylation Reaction of MBH Carbonates: Efficient Construction of Seven-Membered Heterocycles." Organic letters vol. 19,20 (2017): 5609-5612. doi: https://doi.org/10.1021/acs.orglett.7b02742
Chen J, Huang Y. Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic Alkylation Reaction of MBH Carbonates: Efficient Construction of Seven-Membered Heterocycles. Org Lett. 2017 Oct 20;19(20):5609-5612. doi: 10.1021/acs.orglett.7b02742. Epub 2017 Oct 02. PMID: 28968108.
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Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds.

The Journal of organic chemistry

Chen YH, Sun XL, Guan HS, Liu YK.
PMID: 28421761
J Org Chem. 2017 May 05;82(9):4774-4783. doi: 10.1021/acs.joc.7b00461. Epub 2017 Apr 24.

The asymmetric organocatalyzed diversity-oriented one-pot synthesis has been developed to construct chroman-2-one derivatives and other heterocyclic compounds with excellent efficiency and stereoselectivity. The reactions represent a challenging issue, since it altered the inherent selectivity profiles exhibited by the substrates...

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Chen YH, Sun XL, Guan HS, et al. Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds. J Org Chem. 2017;82(9):4774-4783doi: 10.1021/acs.joc.7b00461.
Chen, Y. H., Sun, X. L., Guan, H. S., & Liu, Y. K. (2017). Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds. The Journal of organic chemistry, 82(9), 4774-4783. https://doi.org/10.1021/acs.joc.7b00461
Chen, Ying-Han, et al. "Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds." The Journal of organic chemistry vol. 82,9 (2017): 4774-4783. doi: https://doi.org/10.1021/acs.joc.7b00461
Chen YH, Sun XL, Guan HS, Liu YK. Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds. J Org Chem. 2017 May 05;82(9):4774-4783. doi: 10.1021/acs.joc.7b00461. Epub 2017 Apr 24. PMID: 28421761.
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Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexa-hydro-2H-indazol-2-yl]thia-zol-4(5H)-one.

Acta crystallographica. Section E, Crystallographic communications

Ousidi AN, Itto MY, Auhmani A, Riahi A, Daran JC, Abdelwahed A.
PMID: 27006801
Acta Crystallogr E Crystallogr Commun. 2016 Feb 17;72:334-6. doi: 10.1107/S2056989016002498. eCollection 2016 Mar 01.

The title compound, C13H19N3OS, is a new thia-zolidin-4-one derivative prepared and isolated as the pure (3aS,6R)-diastereisomer from (R)-thio-semicarbazone pulegone. It crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The compound is composed of a hexhydro-indazole...

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Ousidi AN, Itto MY, Auhmani A, et al. Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexa-hydro-2H-indazol-2-yl]thia-zol-4(5H)-one. Acta Crystallogr E Crystallogr Commun. 2016;72:334-6doi: 10.1107/S2056989016002498.
Ousidi, A. N., Itto, M. Y., Auhmani, A., Riahi, A., Daran, J. C., & Abdelwahed, A. (2016). Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexa-hydro-2H-indazol-2-yl]thia-zol-4(5H)-one. Acta crystallographica. Section E, Crystallographic communications, 72334-6. https://doi.org/10.1107/S2056989016002498
Ousidi, Abdellah N'ait, et al. "Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexa-hydro-2H-indazol-2-yl]thia-zol-4(5H)-one." Acta crystallographica. Section E, Crystallographic communications vol. 72 (2016): 334-6. doi: https://doi.org/10.1107/S2056989016002498
Ousidi AN, Itto MY, Auhmani A, Riahi A, Daran JC, Abdelwahed A. Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexa-hydro-2H-indazol-2-yl]thia-zol-4(5H)-one. Acta Crystallogr E Crystallogr Commun. 2016 Feb 17;72:334-6. doi: 10.1107/S2056989016002498. eCollection 2016 Mar 01. PMID: 27006801; PMCID: PMC4778833.
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Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions.

Acta crystallographica. Section C, Structural chemistry

Sagar BK, Harsha KB, Yathirajan HS, Rangappa KS, Rathore RS, Glidewell C.
PMID: 28257028
Acta Crystallogr C Struct Chem. 2017 Mar 01;73:298-304. doi: 10.1107/S205322961700273X. Epub 2017 Feb 23.

In each of 1-(4-fluorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C

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Sagar BK, Harsha KB, Yathirajan HS, et al. Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions. Acta Crystallogr C Struct Chem. 2017;73:298-304doi: 10.1107/S205322961700273X.
Sagar, B. K., Harsha, K. B., Yathirajan, H. S., Rangappa, K. S., Rathore, R. S., & Glidewell, C. (2017). Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions. Acta crystallographica. Section C, Structural chemistry, 73298-304. https://doi.org/10.1107/S205322961700273X
Sagar, Belakavadi K, et al. "Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions." Acta crystallographica. Section C, Structural chemistry vol. 73 (2017): 298-304. doi: https://doi.org/10.1107/S205322961700273X
Sagar BK, Harsha KB, Yathirajan HS, Rangappa KS, Rathore RS, Glidewell C. Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions. Acta Crystallogr C Struct Chem. 2017 Mar 01;73:298-304. doi: 10.1107/S205322961700273X. Epub 2017 Feb 23. PMID: 28257028.
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Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process.

The Journal of organic chemistry

Lam H, Tsoung J, Lautens M.
PMID: 28537390
J Org Chem. 2017 Jun 16;82(12):6089-6099. doi: 10.1021/acs.joc.7b00568. Epub 2017 May 24.

In recent years, our group has been developing multicatalytic reactions for the synthesis of biologically relevant heterocyclic compounds. An efficient dual-metal catalyzed reaction of electron-deficient o-chlorovinylpyridines with o-aminophenylboronic esters to access pyridobenzazepines is described. Combining a Rh

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Lam H, Tsoung J, Lautens M. Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process. J Org Chem. 2017;82(12):6089-6099doi: 10.1021/acs.joc.7b00568.
Lam, H., Tsoung, J., & Lautens, M. (2017). Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process. The Journal of organic chemistry, 82(12), 6089-6099. https://doi.org/10.1021/acs.joc.7b00568
Lam, Heather, et al. "Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process." The Journal of organic chemistry vol. 82,12 (2017): 6089-6099. doi: https://doi.org/10.1021/acs.joc.7b00568
Lam H, Tsoung J, Lautens M. Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process. J Org Chem. 2017 Jun 16;82(12):6089-6099. doi: 10.1021/acs.joc.7b00568. Epub 2017 May 24. PMID: 28537390.
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Correction: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes.

Chemical communications (Cambridge, England)

Goodwin JA, Aponick A.
PMID: 27124721
Chem Commun (Camb). 2016 May 18;52(40):6731. doi: 10.1039/c6cc90121b. Epub 2016 Apr 28.

Correction for 'Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes' by Justin A. Goodwin et al., Chem. Commun., 2015, 51, 8730-8741.

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Goodwin JA, Aponick A. Correction: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chem Commun (Camb). 2016;52(40):6731doi: 10.1039/c6cc90121b.
Goodwin, J. A., & Aponick, A. (2016). Correction: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chemical communications (Cambridge, England), 52(40), 6731. https://doi.org/10.1039/c6cc90121b
Goodwin, Justin A, and Aponick, Aaron. "Correction: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes." Chemical communications (Cambridge, England) vol. 52,40 (2016): 6731. doi: https://doi.org/10.1039/c6cc90121b
Goodwin JA, Aponick A. Correction: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chem Commun (Camb). 2016 May 18;52(40):6731. doi: 10.1039/c6cc90121b. Epub 2016 Apr 28. PMID: 27124721.
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Transcription profiling of the Neurospora crassa response to a group of synthetic (thio)xanthones and a natural acetophenone.

Genomics data

Pedro Gonçalves A, Silva N, Oliveira C, Kowbel DJ, Glass NL, Kijjoa A, Palmeira A, Sousa E, Pinto M, Videira A.
PMID: 26484172
Genom Data. 2015 Feb 20;4:26-32. doi: 10.1016/j.gdata.2015.02.001. eCollection 2015 Jun.

Xanthones are a class of heterocyclic compounds characterized by a dibenzo-γ-pyrone nucleus. Analysis of their mode of action in cells, namely uncovering alterations in gene expression, is important because these compounds have potential therapeutic applications. Thus, we studied the...

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Pedro Gonçalves A, Silva N, Oliveira C, et al. Transcription profiling of the Neurospora crassa response to a group of synthetic (thio)xanthones and a natural acetophenone. Genom Data. 2015;4:26-32doi: 10.1016/j.gdata.2015.02.001.
Pedro Gonçalves, A., Silva, N., Oliveira, C., Kowbel, D. J., Glass, N. L., Kijjoa, A., Palmeira, A., Sousa, E., Pinto, M., & Videira, A. (2015). Transcription profiling of the Neurospora crassa response to a group of synthetic (thio)xanthones and a natural acetophenone. Genomics data, 426-32. https://doi.org/10.1016/j.gdata.2015.02.001
Pedro Gonçalves, A, et al. "Transcription profiling of the Neurospora crassa response to a group of synthetic (thio)xanthones and a natural acetophenone." Genomics data vol. 4 (2015): 26-32. doi: https://doi.org/10.1016/j.gdata.2015.02.001
Pedro Gonçalves A, Silva N, Oliveira C, Kowbel DJ, Glass NL, Kijjoa A, Palmeira A, Sousa E, Pinto M, Videira A. Transcription profiling of the Neurospora crassa response to a group of synthetic (thio)xanthones and a natural acetophenone. Genom Data. 2015 Feb 20;4:26-32. doi: 10.1016/j.gdata.2015.02.001. eCollection 2015 Jun. PMID: 26484172; PMCID: PMC4535624.
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Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations.

Chemical communications (Cambridge, England)

Agasti S, Dey A, Maiti D.
PMID: 28569899
Chem Commun (Camb). 2017 Jun 16;53(49):6544-6556. doi: 10.1039/c7cc02053h.

Heterocyclic compounds are commonly found in the core structures of several pharmaceuticals, natural products, and agrochemicals, thus spurring intensive research for conducting their synthesis in a mild and simpler way. Over the years, a host of different strategies has...

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Agasti S, Dey A, Maiti D. Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations. Chem Commun (Camb). 2017;53(49):6544-6556doi: 10.1039/c7cc02053h.
Agasti, S., Dey, A., & Maiti, D. (2017). Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations. Chemical communications (Cambridge, England), 53(49), 6544-6556. https://doi.org/10.1039/c7cc02053h
Agasti, Soumitra, et al. "Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations." Chemical communications (Cambridge, England) vol. 53,49 (2017): 6544-6556. doi: https://doi.org/10.1039/c7cc02053h
Agasti S, Dey A, Maiti D. Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations. Chem Commun (Camb). 2017 Jun 16;53(49):6544-6556. doi: 10.1039/c7cc02053h. PMID: 28569899.
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Tandem Oxidative C-H Amination and Iodization to Synthesize Difunctional Atropoisomeric P-Stereogenic Phosphinamides.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ma YN, Zhang X, Yang SD.
PMID: 28111873
Chemistry. 2017 Mar 02;23(13):3007-3011. doi: 10.1002/chem.201700218. Epub 2017 Feb 06.

An efficient metal-free tandem intramolecular oxidative C-H amination and iodization of phosphinamide was performed and a series of new phosphorus heterocyclic compounds was obtained. This method provides a concise and highly valuable pathway for the synthesis of difunctional atropoisomeric...

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Ma YN, Zhang X, Yang SD. Tandem Oxidative C-H Amination and Iodization to Synthesize Difunctional Atropoisomeric P-Stereogenic Phosphinamides. Chemistry. 2017;23(13):3007-3011doi: 10.1002/chem.201700218.
Ma, Y. N., Zhang, X., & Yang, S. D. (2017). Tandem Oxidative C-H Amination and Iodization to Synthesize Difunctional Atropoisomeric P-Stereogenic Phosphinamides. Chemistry (Weinheim an der Bergstrasse, Germany), 23(13), 3007-3011. https://doi.org/10.1002/chem.201700218
Ma, Yan-Na, et al. "Tandem Oxidative C-H Amination and Iodization to Synthesize Difunctional Atropoisomeric P-Stereogenic Phosphinamides." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,13 (2017): 3007-3011. doi: https://doi.org/10.1002/chem.201700218
Ma YN, Zhang X, Yang SD. Tandem Oxidative C-H Amination and Iodization to Synthesize Difunctional Atropoisomeric P-Stereogenic Phosphinamides. Chemistry. 2017 Mar 02;23(13):3007-3011. doi: 10.1002/chem.201700218. Epub 2017 Feb 06. PMID: 28111873.
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Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts.

Chemical science

Li BS, Wang Y, Jin Z, Chi YR.
PMID: 29449914
Chem Sci. 2015 Oct 01;6(10):6008-6012. doi: 10.1039/c5sc01972a. Epub 2015 Jul 20.

The addition of an organic catalyst to the ketone moiety of a γ-mono-chloride substituted cyclobutenone destroys its stable, conjugated and nearly planar structure. The C-C bond in the resulting less stable anionic oxy-substituted non-planar intermediate is then activated. The...

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Li BS, Wang Y, Jin Z, et al. Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts. Chem Sci. 2015;6(10):6008-6012doi: 10.1039/c5sc01972a.
Li, B. S., Wang, Y., Jin, Z., & Chi, Y. R. (2015). Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts. Chemical science, 6(10), 6008-6012. https://doi.org/10.1039/c5sc01972a
Li, Bao-Sheng, et al. "Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts." Chemical science vol. 6,10 (2015): 6008-6012. doi: https://doi.org/10.1039/c5sc01972a
Li BS, Wang Y, Jin Z, Chi YR. Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts. Chem Sci. 2015 Oct 01;6(10):6008-6012. doi: 10.1039/c5sc01972a. Epub 2015 Jul 20. PMID: 29449914; PMCID: PMC5669243.
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Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

Beilstein journal of organic chemistry

Wang H, Jiao S, Chen K, Zhang X, Zhao L, Liu D, Zhou Y, Liu H.
PMID: 25977715
Beilstein J Org Chem. 2015 Mar 30;11:416-24. doi: 10.3762/bjoc.11.47. eCollection 2015.

We report a synthetic methodology for the construction of the fused heterocyclic compounds pyrido[2,1-b]quinazolin-9(1H)-ones and pyrrolo[2,1-b]quinazolin-9(1H)-ones through an AgOTf-catalyzed intramolecular alkyne hydroamination reaction. The methodology is applicable to a wide scope of substrates and produces a series of fused...

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Wang H, Jiao S, Chen K, et al. Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions. Beilstein J Org Chem. 2015;11:416-24doi: 10.3762/bjoc.11.47.
Wang, H., Jiao, S., Chen, K., Zhang, X., Zhao, L., Liu, D., Zhou, Y., & Liu, H. (2015). Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions. Beilstein journal of organic chemistry, 11416-24. https://doi.org/10.3762/bjoc.11.47
Wang, Hengshuai, et al. "Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions." Beilstein journal of organic chemistry vol. 11 (2015): 416-24. doi: https://doi.org/10.3762/bjoc.11.47
Wang H, Jiao S, Chen K, Zhang X, Zhao L, Liu D, Zhou Y, Liu H. Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions. Beilstein J Org Chem. 2015 Mar 30;11:416-24. doi: 10.3762/bjoc.11.47. eCollection 2015. PMID: 25977715; PMCID: PMC4419559.
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