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Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom.

Beilstein journal of organic chemistry

Zanella G, Petrović M, Scarpi D, Occhiato EG, Gómez-Bengoa E.
PMID: 33414853
Beilstein J Org Chem. 2020 Dec 15;16:3059-3068. doi: 10.3762/bjoc.16.255. eCollection 2020.

The tandem gold(I)-catalyzed rearrangement/Nazarov reaction of enynyl acetates in which the double bond is embedded in a piperidine ring was computationally and experimentally studied. The theoretical calculations predict that the position of the propargylic acetate substituent has a great...

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Zanella G, Petrović M, Scarpi D, et al. Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom. Beilstein J Org Chem. 2020;16:3059-3068doi: 10.3762/bjoc.16.255.
Zanella, G., Petrović, M., Scarpi, D., Occhiato, E. G., & Gómez-Bengoa, E. (2020). Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom. Beilstein journal of organic chemistry, 163059-3068. https://doi.org/10.3762/bjoc.16.255
Zanella, Giovanna, et al. "Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom." Beilstein journal of organic chemistry vol. 16 (2020): 3059-3068. doi: https://doi.org/10.3762/bjoc.16.255
Zanella G, Petrović M, Scarpi D, Occhiato EG, Gómez-Bengoa E. Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom. Beilstein J Org Chem. 2020 Dec 15;16:3059-3068. doi: 10.3762/bjoc.16.255. eCollection 2020. PMID: 33414853; PMCID: PMC7753109.
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Gene regulation by morpholines and piperidines in the cardiac embryonic stem cell test.

Toxicology and applied pharmacology

Mennen RH, Hallmark N, Pallardy M, Bars R, Tinwell H, Piersma AH.
PMID: 34737147
Toxicol Appl Pharmacol. 2021 Dec 15;433:115781. doi: 10.1016/j.taap.2021.115781. Epub 2021 Oct 29.

The cardiac embryonic stem cell test (ESTc) is an in vitro embryotoxicity screen which uses cardiomyocyte formation as the main differentiation route. Studies are ongoing into whether an improved specification of the biological domain can broaden the applicability of...

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Mennen RH, Hallmark N, Pallardy M, et al. Gene regulation by morpholines and piperidines in the cardiac embryonic stem cell test. Toxicol Appl Pharmacol. 2021;433:115781doi: 10.1016/j.taap.2021.115781.
Mennen, R. H., Hallmark, N., Pallardy, M., Bars, R., Tinwell, H., & Piersma, A. H. (2021). Gene regulation by morpholines and piperidines in the cardiac embryonic stem cell test. Toxicology and applied pharmacology, 433115781. https://doi.org/10.1016/j.taap.2021.115781
Mennen, R H, et al. "Gene regulation by morpholines and piperidines in the cardiac embryonic stem cell test." Toxicology and applied pharmacology vol. 433 (2021): 115781. doi: https://doi.org/10.1016/j.taap.2021.115781
Mennen RH, Hallmark N, Pallardy M, Bars R, Tinwell H, Piersma AH. Gene regulation by morpholines and piperidines in the cardiac embryonic stem cell test. Toxicol Appl Pharmacol. 2021 Dec 15;433:115781. doi: 10.1016/j.taap.2021.115781. Epub 2021 Oct 29. PMID: 34737147.
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Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.

Tetrahedron letters

Gunawan S, Bedard N, Foley C, Hulme C.
PMID: 34737462
Tetrahedron Lett. 2021 Apr 13;69. doi: 10.1016/j.tetlet.2021.152978. Epub 2021 Mar 17.

This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)

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Gunawan S, Bedard N, Foley C, et al. Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners. Tetrahedron Lett. 2021;69doi: 10.1016/j.tetlet.2021.152978.
Gunawan, S., Bedard, N., Foley, C., & Hulme, C. (2021). Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners. Tetrahedron letters, 69. https://doi.org/10.1016/j.tetlet.2021.152978
Gunawan, Steven, et al. "Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners." Tetrahedron letters vol. 69 (2021). doi: https://doi.org/10.1016/j.tetlet.2021.152978
Gunawan S, Bedard N, Foley C, Hulme C. Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners. Tetrahedron Lett. 2021 Apr 13;69. doi: 10.1016/j.tetlet.2021.152978. Epub 2021 Mar 17. PMID: 34737462; PMCID: PMC8562708.
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Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo- and enantioselectivity, and reaction mechanism.

Journal of the American Chemical Society

Hong S, Kawaoka AM, Marks TJ.
PMID: 14677980
J Am Chem Soc. 2003 Dec 24;125(51):15878-92. doi: 10.1021/ja036266y.

Organolanthanide complexes of the general type Cp'(2)LnCH(TMS)(2) (Cp' = eta(5)-Me(5)C(5); Ln = La, Sm, Y; TMS = SiMe(3)) and CGCSmN(TMS)(2) (CGC = Me(2)Si(eta(5)-Me(4)C(5))((t)()BuN)) serve as effective precatalysts for the rapid, regioselective, and highly diastereoselective intramolecular hydroamination/cyclization of primary and...

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Hong S, Kawaoka AM, Marks TJ. Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo- and enantioselectivity, and reaction mechanism. J Am Chem Soc. 2003;125(51):15878-92doi: 10.1021/ja036266y.
Hong, S., Kawaoka, A. M., & Marks, T. J. (2003). Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo- and enantioselectivity, and reaction mechanism. Journal of the American Chemical Society, 125(51), 15878-92. https://doi.org/10.1021/ja036266y
Hong, Sukwon, et al. "Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo- and enantioselectivity, and reaction mechanism." Journal of the American Chemical Society vol. 125,51 (2003): 15878-92. doi: https://doi.org/10.1021/ja036266y
Hong S, Kawaoka AM, Marks TJ. Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo- and enantioselectivity, and reaction mechanism. J Am Chem Soc. 2003 Dec 24;125(51):15878-92. doi: 10.1021/ja036266y. PMID: 14677980.
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Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate.

Chemistry (Weinheim an der Bergstrasse, Germany)

Leverenz M, Masson G, Pardo DG, Cossy J.
PMID: 34643301
Chemistry. 2021 Nov 25;27(66):16325-16328. doi: 10.1002/chem.202102739. Epub 2021 Oct 21.

α-Trifluoromethyl azocanes are accessible from 2-(trifluoropropan-2-ol) piperidines by metal-free ring-expansion involving a bicyclic azetidinium intermediate. The opening of the azetidinium intermediate was achieved by various nucleophiles (amines, alcoholates, carboxylates, phosphonates, halides and pseudo-halides) with an excellent regio- diastereo- and...

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Leverenz M, Masson G, Pardo DG, et al. Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate. Chemistry. 2021;27(66):16325-16328doi: 10.1002/chem.202102739.
Leverenz, M., Masson, G., Pardo, D. G., & Cossy, J. (2021). Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate. Chemistry (Weinheim an der Bergstrasse, Germany), 27(66), 16325-16328. https://doi.org/10.1002/chem.202102739
Leverenz, Malte, et al. "Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 27,66 (2021): 16325-16328. doi: https://doi.org/10.1002/chem.202102739
Leverenz M, Masson G, Pardo DG, Cossy J. Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate. Chemistry. 2021 Nov 25;27(66):16325-16328. doi: 10.1002/chem.202102739. Epub 2021 Oct 21. PMID: 34643301.
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Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions.

Angewandte Chemie (International ed. in English)

List B, Grossmann O, Maji R, Aukland MH, Lee S.
PMID: 34897932
Angew Chem Int Ed Engl. 2021 Dec 12; doi: 10.1002/anie.202115036. Epub 2021 Dec 12.

Strong and confined imidodiphosphorimidate (IDPi) catalysts enable highly enantioselective substitutions of cyclic, aliphatic hemiaminal ethers with enol silanes. 2-Substituted pyrrolidines, piperidines, and azepanes are obtained with high enantioselectivities, and the method displays a broad tolerance of various enol silane...

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List B, Grossmann O, Maji R, et al. Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions. Angew Chem Int Ed Engl. 2021;doi: 10.1002/anie.202115036.
List, B., Grossmann, O., Maji, R., Aukland, M. H., & Lee, S. (2021). Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions. Angewandte Chemie (International ed. in English), . https://doi.org/10.1002/anie.202115036
List, Benjamin, et al. "Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions." Angewandte Chemie (International ed. in English) vol. (2021). doi: https://doi.org/10.1002/anie.202115036
List B, Grossmann O, Maji R, Aukland MH, Lee S. Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions. Angew Chem Int Ed Engl. 2021 Dec 12; doi: 10.1002/anie.202115036. Epub 2021 Dec 12. PMID: 34897932.
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Single point activation of pyridines enables reductive hydroxymethylation.

Chemical science

Marinic B, Hepburn HB, Grozavu A, Dow M, Donohoe TJ.
PMID: 34163807
Chem Sci. 2020 Nov 16;12(2):742-746. doi: 10.1039/d0sc05656a.

The single point activation of pyridines, using an electron-deficient benzyl group, facilitates the ruthenium-catalysed dearomative functionalisation of a range of electronically diverse pyridine derivatives. This transformation delivers hydroxymethylated piperidines in good yields, allowing rapid access to medicinally relevant small...

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Marinic B, Hepburn HB, Grozavu A, et al. Single point activation of pyridines enables reductive hydroxymethylation. Chem Sci. 2020;12(2):742-746doi: 10.1039/d0sc05656a.
Marinic, B., Hepburn, H. B., Grozavu, A., Dow, M., & Donohoe, T. J. (2020). Single point activation of pyridines enables reductive hydroxymethylation. Chemical science, 12(2), 742-746. https://doi.org/10.1039/d0sc05656a
Marinic, Bruno, et al. "Single point activation of pyridines enables reductive hydroxymethylation." Chemical science vol. 12,2 (2020): 742-746. doi: https://doi.org/10.1039/d0sc05656a
Marinic B, Hepburn HB, Grozavu A, Dow M, Donohoe TJ. Single point activation of pyridines enables reductive hydroxymethylation. Chem Sci. 2020 Nov 16;12(2):742-746. doi: 10.1039/d0sc05656a. PMID: 34163807; PMCID: PMC8178984.
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CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE.

Heterocycles

Beng TK, Gawley RE.
PMID: 22408286
Heterocycles. 2012 Jan 01;84(2):697-718. doi: 10.3987/com-11-s(p)45.

The diastereoselective synthesis of trans-2,6-disubstituted piperidines has been rendered enantioselective by incorporating a catalytic dynamic resolution into the first alkylation step. The method has been applied to the synthesis of (-)-epidihydropinidine and (+)-trans-lupetidine.

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Beng TK, Gawley RE. CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE. Heterocycles. 2012;84(2):697-718doi: 10.3987/com-11-s(p)45.
Beng, T. K., & Gawley, R. E. (2012). CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE. Heterocycles, 84(2), 697-718. https://doi.org/10.3987/com-11-s(p)45
Beng, Timothy K, and Gawley, Robert E. "CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE." Heterocycles vol. 84,2 (2012): 697-718. doi: https://doi.org/10.3987/com-11-s(p)45
Beng TK, Gawley RE. CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE. Heterocycles. 2012 Jan 01;84(2):697-718. doi: 10.3987/com-11-s(p)45. PMID: 22408286; PMCID: PMC3295593.
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Showing 229 to 236 of 236 entries