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Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines.

Organic letters

Dave R, Sasaki NA.
PMID: 14703339
Org Lett. 2004 Jan 08;6(1):15-8. doi: 10.1021/ol035998s.

[reaction: see text] (3R,5R)-1 R1 & R2 = TBDPS, (3S,5R)-2 R1 = Bn,R2 = TBDPS, (3S,5S)-3 R2 & R2 = Bn. trans-3,5-Bis(benzyl/tert-butyldiphenylsilyloxymethyl)morpholines, promising candidates for the C(2)-symmetric class of chiral reagents, were prepared with excellent optical purity. A key...

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Dave R, Sasaki NA. Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines. Org Lett. 2004;6(1):15-8doi: 10.1021/ol035998s.
Dave, R., & Sasaki, N. A. (2004). Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines. Organic letters, 6(1), 15-8. https://doi.org/10.1021/ol035998s
Dave, Rajesh, and Sasaki, N André. "Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines." Organic letters vol. 6,1 (2004): 15-8. doi: https://doi.org/10.1021/ol035998s
Dave R, Sasaki NA. Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines. Org Lett. 2004 Jan 08;6(1):15-8. doi: 10.1021/ol035998s. PMID: 14703339.
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Diastereoselective synthesis of enantiopure morpholines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives.

The Journal of organic chemistry

Pedrosa R, Andrés C, Mendiguchía P, Nieto J.
PMID: 17081016
J Org Chem. 2006 Nov 10;71(23):8854-63. doi: 10.1021/jo061547k.

Enantiopure morpholine derivatives have been prepared by selenocyclofunctionalization of chiral 3-allyl-2-hydroxymethyl-substituted perhydro-1,3-benzoxazine derivatives. The cyclization occurs in high yields and diastereoselection, although the temperature of the reaction and the structure of the substituent at C-2 and the substitution pattern...

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Pedrosa R, Andrés C, Mendiguchía P, et al. Diastereoselective synthesis of enantiopure morpholines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives. J Org Chem. 2006;71(23):8854-63doi: 10.1021/jo061547k.
Pedrosa, R., Andrés, C., Mendiguchía, P., & Nieto, J. (2006). Diastereoselective synthesis of enantiopure morpholines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives. The Journal of organic chemistry, 71(23), 8854-63. https://doi.org/10.1021/jo061547k
Pedrosa, Rafael, et al. "Diastereoselective synthesis of enantiopure morpholines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives." The Journal of organic chemistry vol. 71,23 (2006): 8854-63. doi: https://doi.org/10.1021/jo061547k
Pedrosa R, Andrés C, Mendiguchía P, Nieto J. Diastereoselective synthesis of enantiopure morpholines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives. J Org Chem. 2006 Nov 10;71(23):8854-63. doi: 10.1021/jo061547k. PMID: 17081016.
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Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine.

Inorganic chemistry

Kim J, Singh RP, Shreeve JM.
PMID: 15106985
Inorg Chem. 2004 May 03;43(9):2960-6. doi: 10.1021/ic049916n.

N-Alkyl- and N-fluoroalkyl-substituted oxazolidinium- and morpholinium-based quaternary salts and ionic liquids have been synthesized and characterized. Reactions of N-methyloxazolidine (1) or N-methylmorpholine (2) with 3-fluoropropyl bromide or iodopropane in THF at 25 degrees C gave the quaternary salts (3a,b,...

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Kim J, Singh RP, Shreeve JM. Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine. Inorg Chem. 2004;43(9):2960-6doi: 10.1021/ic049916n.
Kim, J., Singh, R. P., & Shreeve, J. M. (2004). Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine. Inorganic chemistry, 43(9), 2960-6. https://doi.org/10.1021/ic049916n
Kim, Jinwi, et al. "Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine." Inorganic chemistry vol. 43,9 (2004): 2960-6. doi: https://doi.org/10.1021/ic049916n
Kim J, Singh RP, Shreeve JM. Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine. Inorg Chem. 2004 May 03;43(9):2960-6. doi: 10.1021/ic049916n. PMID: 15106985.
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Heterocycles via intramolecular platinum-catalyzed propargylic substitution.

Tetrahedron

Liang Q, De Brabander JK.
PMID: 21731116
Tetrahedron. 2011 Jul 08;67(27):5046-5053. doi: 10.1016/j.tet.2011.03.115.

We report a Pt(II)-catalyzed cyclization of nucleophile-tethered propargylic acetates yielding substituted heterocycles containing multiple heteroatoms including morpholines, dioxanes and sulfamates with high cis-selectivity.

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Liang Q, De Brabander JK. Heterocycles via intramolecular platinum-catalyzed propargylic substitution. Tetrahedron. 2011;67(27):5046-5053doi: 10.1016/j.tet.2011.03.115.
Liang, Q., & De Brabander, J. K. (2011). Heterocycles via intramolecular platinum-catalyzed propargylic substitution. Tetrahedron, 67(27), 5046-5053. https://doi.org/10.1016/j.tet.2011.03.115
Liang, Qiren, and De Brabander, Jef K. "Heterocycles via intramolecular platinum-catalyzed propargylic substitution." Tetrahedron vol. 67,27 (2011): 5046-5053. doi: https://doi.org/10.1016/j.tet.2011.03.115
Liang Q, De Brabander JK. Heterocycles via intramolecular platinum-catalyzed propargylic substitution. Tetrahedron. 2011 Jul 08;67(27):5046-5053. doi: 10.1016/j.tet.2011.03.115. PMID: 21731116; PMCID: PMC3126105.
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Synthesis and Evaluation of Benzophenone-N-ethyl Morpholine Ethers as Anti-inflammatory Agents.

International journal of biomedical science : IJBS

Khanum SA, Begum BA, Girish V, Khanum NF.
PMID: 23675177
Int J Biomed Sci. 2010 Mar;6(1):60-5.

The synthesis of hydroxy benzophenones and benzophenone-N-ethyl morpholine ethers and the results of anti-inflammatory activity in vivo are described. The structures of the compounds were elucidated by IR, (1)H-NMR, mass spectroscopy and the elementary analysis. The anti-inflammatory activity of...

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Khanum SA, Begum BA, Girish V, et al. Synthesis and Evaluation of Benzophenone-N-ethyl Morpholine Ethers as Anti-inflammatory Agents. Int J Biomed Sci. 2010;6(1):60-5
Khanum, S. A., Begum, B. A., Girish, V., & Khanum, N. F. (2010). Synthesis and Evaluation of Benzophenone-N-ethyl Morpholine Ethers as Anti-inflammatory Agents. International journal of biomedical science : IJBS, 6(1), 60-5.
Khanum, Shaukath A, et al. "Synthesis and Evaluation of Benzophenone-N-ethyl Morpholine Ethers as Anti-inflammatory Agents." International journal of biomedical science : IJBS vol. 6,1 (2010): 60-5.
Khanum SA, Begum BA, Girish V, Khanum NF. Synthesis and Evaluation of Benzophenone-N-ethyl Morpholine Ethers as Anti-inflammatory Agents. Int J Biomed Sci. 2010 Mar;6(1):60-5. PMID: 23675177; PMCID: PMC3614727.
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A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines.

Organic letters

Aubineau T, Cossy J.
PMID: 30452270
Org Lett. 2018 Dec 07;20(23):7419-7423. doi: 10.1021/acs.orglett.8b03141. Epub 2018 Nov 19.

The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to...

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Aubineau T, Cossy J. A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines. Org Lett. 2018;20(23):7419-7423doi: 10.1021/acs.orglett.8b03141.
Aubineau, T., & Cossy, J. (2018). A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines. Organic letters, 20(23), 7419-7423. https://doi.org/10.1021/acs.orglett.8b03141
Aubineau, Thomas, and Cossy, Janine. "A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines." Organic letters vol. 20,23 (2018): 7419-7423. doi: https://doi.org/10.1021/acs.orglett.8b03141
Aubineau T, Cossy J. A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines. Org Lett. 2018 Dec 07;20(23):7419-7423. doi: 10.1021/acs.orglett.8b03141. Epub 2018 Nov 19. PMID: 30452270.
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Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines.

Organic letters

Duchamp E, Simard BD, Hanessian S.
PMID: 31240939
Org Lett. 2019 Sep 06;21(17):6593-6596. doi: 10.1021/acs.orglett.9b01842. Epub 2019 Jun 26.

A new methodology to synthesize 2,6-di-, and 2,2',6-trisubstituted morpholines via the reduction of oxabicyclic tetrazoles under mild conditions is described. The reaction proved successful for a wide range of tetrazoles, including sterically encumbered ones harboring

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Duchamp E, Simard BD, Hanessian S. Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines. Org Lett. 2019;21(17):6593-6596doi: 10.1021/acs.orglett.9b01842.
Duchamp, E., Simard, B. D., & Hanessian, S. (2019). Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines. Organic letters, 21(17), 6593-6596. https://doi.org/10.1021/acs.orglett.9b01842
Duchamp, Edouard, et al. "Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines." Organic letters vol. 21,17 (2019): 6593-6596. doi: https://doi.org/10.1021/acs.orglett.9b01842
Duchamp E, Simard BD, Hanessian S. Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines. Org Lett. 2019 Sep 06;21(17):6593-6596. doi: 10.1021/acs.orglett.9b01842. Epub 2019 Jun 26. PMID: 31240939.
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Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.

Chemical science

Li M, Zhang J, Zou Y, Zhou F, Zhang Z, Zhang W.
PMID: 34909146
Chem Sci. 2021 Oct 28;12(45):15061-15066. doi: 10.1039/d1sc04288b. eCollection 2021 Nov 24.

Asymmetric hydrogenation of unsaturated morpholines has been developed by using a bisphosphine-rhodium catalyst bearing a large bite angle. With this approach, a variety of 2-substituted chiral morpholines could be obtained in quantitative yields and with excellent enantioselectivities (up to...

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Li M, Zhang J, Zou Y, et al. Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines. Chem Sci. 2021;12(45):15061-15066doi: 10.1039/d1sc04288b.
Li, M., Zhang, J., Zou, Y., Zhou, F., Zhang, Z., & Zhang, W. (2021). Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines. Chemical science, 12(45), 15061-15066. https://doi.org/10.1039/d1sc04288b
Li, Mingxu, et al. "Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines." Chemical science vol. 12,45 (2021): 15061-15066. doi: https://doi.org/10.1039/d1sc04288b
Li M, Zhang J, Zou Y, Zhou F, Zhang Z, Zhang W. Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines. Chem Sci. 2021 Oct 28;12(45):15061-15066. doi: 10.1039/d1sc04288b. eCollection 2021 Nov 24. PMID: 34909146; PMCID: PMC8612400.
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Diastereoselective protocols for the synthesis of 2,3-trans- and 2,3-cis-6-methoxy-morpholine-2-carboxylic acid derivatives.

The Journal of organic chemistry

Penso M, Foschi F, Pellegrino S, Testa A, Gelmi ML.
PMID: 22394367
J Org Chem. 2012 Apr 06;77(7):3454-61. doi: 10.1021/jo300221y. Epub 2012 Mar 21.

Two diastereoselective and straightforward protocols for the high-yielding synthesis of 2,3-trans- and 2,3-cis-6-methoxy-3-substituted morpholine-2-carboxylic esters were realized in few steps, through the condensation between 5,6-diethoxy-5,6-dimethyl-1,4-dioxan-2-one and an appropriate imine, which is the key reaction to control the C2-C3 relative...

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Penso M, Foschi F, Pellegrino S, et al. Diastereoselective protocols for the synthesis of 2,3-trans- and 2,3-cis-6-methoxy-morpholine-2-carboxylic acid derivatives. J Org Chem. 2012;77(7):3454-61doi: 10.1021/jo300221y.
Penso, M., Foschi, F., Pellegrino, S., Testa, A., & Gelmi, M. L. (2012). Diastereoselective protocols for the synthesis of 2,3-trans- and 2,3-cis-6-methoxy-morpholine-2-carboxylic acid derivatives. The Journal of organic chemistry, 77(7), 3454-61. https://doi.org/10.1021/jo300221y
Penso, Michele, et al. "Diastereoselective protocols for the synthesis of 2,3-trans- and 2,3-cis-6-methoxy-morpholine-2-carboxylic acid derivatives." The Journal of organic chemistry vol. 77,7 (2012): 3454-61. doi: https://doi.org/10.1021/jo300221y
Penso M, Foschi F, Pellegrino S, Testa A, Gelmi ML. Diastereoselective protocols for the synthesis of 2,3-trans- and 2,3-cis-6-methoxy-morpholine-2-carboxylic acid derivatives. J Org Chem. 2012 Apr 06;77(7):3454-61. doi: 10.1021/jo300221y. Epub 2012 Mar 21. PMID: 22394367.
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Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a log.

ACS medicinal chemistry letters

Degorce SL, Bodnarchuk MS, Scott JS.
PMID: 31417667
ACS Med Chem Lett. 2019 Jul 18;10(8):1198-1204. doi: 10.1021/acsmedchemlett.9b00248. eCollection 2019 Aug 08.

We have conducted an analysis of azaspiro[3.3]heptanes used as replacements for morpholines, piperidines, and piperazines in a medicinal chemistry context. In most cases, introducing a spirocyclic center lowered the measured log

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Degorce SL, Bodnarchuk MS, Scott JS. Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a log. ACS Med Chem Lett. 2019;10(8):1198-1204doi: 10.1021/acsmedchemlett.9b00248.
Degorce, S. L., Bodnarchuk, M. S., & Scott, J. S. (2019). Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a log. ACS medicinal chemistry letters, 10(8), 1198-1204. https://doi.org/10.1021/acsmedchemlett.9b00248
Degorce, Sébastien L, et al. "Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a log." ACS medicinal chemistry letters vol. 10,8 (2019): 1198-1204. doi: https://doi.org/10.1021/acsmedchemlett.9b00248
Degorce SL, Bodnarchuk MS, Scott JS. Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a log. ACS Med Chem Lett. 2019 Jul 18;10(8):1198-1204. doi: 10.1021/acsmedchemlett.9b00248. eCollection 2019 Aug 08. PMID: 31417667; PMCID: PMC6693472.
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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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Initial Optimization of a New Series of γ-Secretase Modulators Derived from a Triterpene Glycoside.

ACS medicinal chemistry letters

Fuller NO, Hubbs JL, Austin WF, Creaser SP, McKee TD, Loureiro RM, Tate B, Xia W, Ives JL, Findeis MA, Bronk BS.
PMID: 24900406
ACS Med Chem Lett. 2012 Aug 29;3(11):908-13. doi: 10.1021/ml300256p. eCollection 2012 Nov 08.

The discovery of a new series of γ-secretase modulators is disclosed. Starting from a triterpene glycoside γ-secretase modulator that gave a very low brain-to-plasma ratio, initial SAR and optimization involved replacement of a pendant sugar with a series of...

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Fuller NO, Hubbs JL, Austin WF, et al. Initial Optimization of a New Series of γ-Secretase Modulators Derived from a Triterpene Glycoside. ACS Med Chem Lett. 2012;3(11):908-13doi: 10.1021/ml300256p.
Fuller, N. O., Hubbs, J. L., Austin, W. F., Creaser, S. P., McKee, T. D., Loureiro, R. M., Tate, B., Xia, W., Ives, J. L., Findeis, M. A., & Bronk, B. S. (2012). Initial Optimization of a New Series of γ-Secretase Modulators Derived from a Triterpene Glycoside. ACS medicinal chemistry letters, 3(11), 908-13. https://doi.org/10.1021/ml300256p
Fuller, Nathan O, et al. "Initial Optimization of a New Series of γ-Secretase Modulators Derived from a Triterpene Glycoside." ACS medicinal chemistry letters vol. 3,11 (2012): 908-13. doi: https://doi.org/10.1021/ml300256p
Fuller NO, Hubbs JL, Austin WF, Creaser SP, McKee TD, Loureiro RM, Tate B, Xia W, Ives JL, Findeis MA, Bronk BS. Initial Optimization of a New Series of γ-Secretase Modulators Derived from a Triterpene Glycoside. ACS Med Chem Lett. 2012 Aug 29;3(11):908-13. doi: 10.1021/ml300256p. eCollection 2012 Nov 08. PMID: 24900406; PMCID: PMC4025870.
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Showing 1 to 12 of 42 entries