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Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines.

Organic letters

Landge VG, Midya SP, Rana J, Shinde DR, Balaraman E.
PMID: 27700123
Org Lett. 2016 Oct 21;18(20):5252-5255. doi: 10.1021/acs.orglett.6b02549. Epub 2016 Oct 04.

A unified strategy for cobalt-catalyzed ortho-C-H bond alkynylation of benzylamines is reported. Simple, commercially available CoBr

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Landge VG, Midya SP, Rana J, et al. Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines. Org Lett. 2016;18(20):5252-5255doi: 10.1021/acs.orglett.6b02549.
Landge, V. G., Midya, S. P., Rana, J., Shinde, D. R., & Balaraman, E. (2016). Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines. Organic letters, 18(20), 5252-5255. https://doi.org/10.1021/acs.orglett.6b02549
Landge, Vinod G, et al. "Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines." Organic letters vol. 18,20 (2016): 5252-5255. doi: https://doi.org/10.1021/acs.orglett.6b02549
Landge VG, Midya SP, Rana J, Shinde DR, Balaraman E. Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines. Org Lett. 2016 Oct 21;18(20):5252-5255. doi: 10.1021/acs.orglett.6b02549. Epub 2016 Oct 04. PMID: 27700123.
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Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia.

Organic & biomolecular chemistry

Gopalaiah K, Saini A, Devi A.
PMID: 28660261
Org Biomol Chem. 2017 Jul 21;15(27):5781-5789. doi: 10.1039/c7ob01159h. Epub 2017 Jun 29.

A novel approach to construct 2-aryl/heteroaryl quinazolines was developed through an iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines under aerobic oxidative conditions. The reaction proceeds via the formation of N-benzylidenebenzylamines followed by oxidative trapping of ammonia/intramolecular cyclization in...

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Gopalaiah K, Saini A, Devi A. Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Org Biomol Chem. 2017;15(27):5781-5789doi: 10.1039/c7ob01159h.
Gopalaiah, K., Saini, A., & Devi, A. (2017). Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Organic & biomolecular chemistry, 15(27), 5781-5789. https://doi.org/10.1039/c7ob01159h
Gopalaiah, Kovuru, et al. "Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia." Organic & biomolecular chemistry vol. 15,27 (2017): 5781-5789. doi: https://doi.org/10.1039/c7ob01159h
Gopalaiah K, Saini A, Devi A. Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Org Biomol Chem. 2017 Jul 21;15(27):5781-5789. doi: 10.1039/c7ob01159h. Epub 2017 Jun 29. PMID: 28660261.
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Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C-N Bond Activation.

Chemistry (Weinheim an der Bergstrasse, Germany)

Yu H, Hu B, Huang H.
PMID: 29517114
Chemistry. 2018 May 17;24(28):7114-7117. doi: 10.1002/chem.201800543. Epub 2018 Apr 26.

A nickel-catalyzed alkylarylation of active alkenes with tertiary benzylamines was achieved by charge-transfer-complex promoted C-N bond activation. The reaction proceeded through initial Ni-catalyzed C-N bond activation, followed by sequential radical addition, redox and proton abstraction with cleaved amine moiety...

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Yu H, Hu B, Huang H. Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C-N Bond Activation. Chemistry. 2018;24(28):7114-7117doi: 10.1002/chem.201800543.
Yu, H., Hu, B., & Huang, H. (2018). Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C-N Bond Activation. Chemistry (Weinheim an der Bergstrasse, Germany), 24(28), 7114-7117. https://doi.org/10.1002/chem.201800543
Yu, Hui, et al. "Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C-N Bond Activation." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,28 (2018): 7114-7117. doi: https://doi.org/10.1002/chem.201800543
Yu H, Hu B, Huang H. Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C-N Bond Activation. Chemistry. 2018 May 17;24(28):7114-7117. doi: 10.1002/chem.201800543. Epub 2018 Apr 26. PMID: 29517114.
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Small Molecule Lysyl Oxidase-like 2 (LOXL2) Inhibitors: The Identification of an Inhibitor Selective for LOXL2 over LOX.

ACS medicinal chemistry letters

Hutchinson JH, Rowbottom MW, Lonergan D, Darlington J, Prodanovich P, King CD, Evans JF, Bain G.
PMID: 28435530
ACS Med Chem Lett. 2017 Mar 01;8(4):423-427. doi: 10.1021/acsmedchemlett.7b00014. eCollection 2017 Apr 13.

Two series of novel LOXL2 enzyme inhibitors are described: benzylamines substituted with electron withdrawing groups at the

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Hutchinson JH, Rowbottom MW, Lonergan D, et al. Small Molecule Lysyl Oxidase-like 2 (LOXL2) Inhibitors: The Identification of an Inhibitor Selective for LOXL2 over LOX. ACS Med Chem Lett. 2017;8(4):423-427doi: 10.1021/acsmedchemlett.7b00014.
Hutchinson, J. H., Rowbottom, M. W., Lonergan, D., Darlington, J., Prodanovich, P., King, C. D., Evans, J. F., & Bain, G. (2017). Small Molecule Lysyl Oxidase-like 2 (LOXL2) Inhibitors: The Identification of an Inhibitor Selective for LOXL2 over LOX. ACS medicinal chemistry letters, 8(4), 423-427. https://doi.org/10.1021/acsmedchemlett.7b00014
Hutchinson, John H, et al. "Small Molecule Lysyl Oxidase-like 2 (LOXL2) Inhibitors: The Identification of an Inhibitor Selective for LOXL2 over LOX." ACS medicinal chemistry letters vol. 8,4 (2017): 423-427. doi: https://doi.org/10.1021/acsmedchemlett.7b00014
Hutchinson JH, Rowbottom MW, Lonergan D, Darlington J, Prodanovich P, King CD, Evans JF, Bain G. Small Molecule Lysyl Oxidase-like 2 (LOXL2) Inhibitors: The Identification of an Inhibitor Selective for LOXL2 over LOX. ACS Med Chem Lett. 2017 Mar 01;8(4):423-427. doi: 10.1021/acsmedchemlett.7b00014. eCollection 2017 Apr 13. PMID: 28435530; PMCID: PMC5392766.
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Synthesis and Octopaminergic Agonist Activity of 2-(Substituted benzylamino)-2-thiazolines.

Bioscience, biotechnology, and biochemistry

Hirashima A, Yoshii Y, Eto M.
PMID: 27286378
Biosci Biotechnol Biochem. 1992 Jan;56(7):1062-5. doi: 10.1271/bbb.56.1062.

2-(Substituted benzylamino)-2-thiazolines (SBAT) were synthesized by a hydrochloric acid-catalyzed cyclization of the corresponding thioureas, using a reaction of 2-methylthio-2-thiazoline with substituted benzylamines or by alkylating 2-amino-2-thiazoline. 2-(Alkylthio)-2-thiazolines were obtained by alkylating 2-mercaptothiazoline. Most of the SBAT compounds activated adenylate...

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Hirashima A, Yoshii Y, Eto M. Synthesis and Octopaminergic Agonist Activity of 2-(Substituted benzylamino)-2-thiazolines. Biosci Biotechnol Biochem. 1992;56(7):1062-5doi: 10.1271/bbb.56.1062.
Hirashima, A., Yoshii, Y., & Eto, M. (1992). Synthesis and Octopaminergic Agonist Activity of 2-(Substituted benzylamino)-2-thiazolines. Bioscience, biotechnology, and biochemistry, 56(7), 1062-5. https://doi.org/10.1271/bbb.56.1062
Hirashima, A, et al. "Synthesis and Octopaminergic Agonist Activity of 2-(Substituted benzylamino)-2-thiazolines." Bioscience, biotechnology, and biochemistry vol. 56,7 (1992): 1062-5. doi: https://doi.org/10.1271/bbb.56.1062
Hirashima A, Yoshii Y, Eto M. Synthesis and Octopaminergic Agonist Activity of 2-(Substituted benzylamino)-2-thiazolines. Biosci Biotechnol Biochem. 1992 Jan;56(7):1062-5. doi: 10.1271/bbb.56.1062. PMID: 27286378.
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Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography.

Analytical chemistry

Fischer H, Gyllenhaal O, Vessman J, Albert K.
PMID: 12585493
Anal Chem. 2003 Feb 01;75(3):622-6. doi: 10.1021/ac020527p.

In the recent years, it has repeatedly been stated that amines react with CO2 and can therefore not be chromatographed under supercritical conditions with CO2. The aim of the present work is to elucidate the structural requirements and conditions...

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Fischer H, Gyllenhaal O, Vessman J, et al. Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography. Anal Chem. 2003;75(3):622-6doi: 10.1021/ac020527p.
Fischer, H., Gyllenhaal, O., Vessman, J., & Albert, K. (2003). Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography. Analytical chemistry, 75(3), 622-6. https://doi.org/10.1021/ac020527p
Fischer, Holger, et al. "Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography." Analytical chemistry vol. 75,3 (2003): 622-6. doi: https://doi.org/10.1021/ac020527p
Fischer H, Gyllenhaal O, Vessman J, Albert K. Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography. Anal Chem. 2003 Feb 01;75(3):622-6. doi: 10.1021/ac020527p. PMID: 12585493.
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Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles.

Organic letters

Oña-Burgos P, Fernández I, Roces L, Torre-Fernández L, García-Granda S, López-Ortiz F.
PMID: 18582070
Org Lett. 2008 Aug 07;10(15):3195-8. doi: 10.1021/ol801027p. Epub 2008 Jun 27.

Pop-directed asymmetric deprotonation of benzylic amines using [n-BuLi/(-)-sparteine] provides an efficient method for the synthesis of chiral NC alpha and NC alpha,alpha' derivatives with total selectivity with respect to competing allylic and ortho lithiation. The method described herein offers...

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Oña-Burgos P, Fernández I, Roces L, et al. Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles. Org Lett. 2008;10(15):3195-8doi: 10.1021/ol801027p.
Oña-Burgos, P., Fernández, I., Roces, L., Torre-Fernández, L., García-Granda, S., & López-Ortiz, F. (2008). Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles. Organic letters, 10(15), 3195-8. https://doi.org/10.1021/ol801027p
Oña-Burgos, Pascual, et al. "Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles." Organic letters vol. 10,15 (2008): 3195-8. doi: https://doi.org/10.1021/ol801027p
Oña-Burgos P, Fernández I, Roces L, Torre-Fernández L, García-Granda S, López-Ortiz F. Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles. Org Lett. 2008 Aug 07;10(15):3195-8. doi: 10.1021/ol801027p. Epub 2008 Jun 27. PMID: 18582070.
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Oxidative cleavage of benzylic C-N bonds under metal-free conditions.

Organic & biomolecular chemistry

Gong JL, Qi X, Wei D, Feng JB, Wu XF.
PMID: 25156588
Org Biomol Chem. 2014 Oct 14;12(38):7486-8. doi: 10.1039/c4ob01633e.

An interesting procedure for the oxidative cleavage of benzylic C-N bonds has been developed. Using TBAI as the catalyst and H2O2 as the oxidant, various benzylamines were transformed into their corresponding aromatic aldehydes in moderate to good yields. Notably,...

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Gong JL, Qi X, Wei D, et al. Oxidative cleavage of benzylic C-N bonds under metal-free conditions. Org Biomol Chem. 2014;12(38):7486-8doi: 10.1039/c4ob01633e.
Gong, J. L., Qi, X., Wei, D., Feng, J. B., & Wu, X. F. (2014). Oxidative cleavage of benzylic C-N bonds under metal-free conditions. Organic & biomolecular chemistry, 12(38), 7486-8. https://doi.org/10.1039/c4ob01633e
Gong, Jin-Long, et al. "Oxidative cleavage of benzylic C-N bonds under metal-free conditions." Organic & biomolecular chemistry vol. 12,38 (2014): 7486-8. doi: https://doi.org/10.1039/c4ob01633e
Gong JL, Qi X, Wei D, Feng JB, Wu XF. Oxidative cleavage of benzylic C-N bonds under metal-free conditions. Org Biomol Chem. 2014 Oct 14;12(38):7486-8. doi: 10.1039/c4ob01633e. PMID: 25156588.
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Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams.

Organic letters

Zhang C, Ding Y, Gao Y, Li S, Li G.
PMID: 29683329
Org Lett. 2018 May 04;20(9):2595-2598. doi: 10.1021/acs.orglett.8b00786. Epub 2018 Apr 23.

A protocol for palladium-catalyzed C-H carbonylation of readily available free primary benzylamines using NH

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Zhang C, Ding Y, Gao Y, et al. Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams. Org Lett. 2018;20(9):2595-2598doi: 10.1021/acs.orglett.8b00786.
Zhang, C., Ding, Y., Gao, Y., Li, S., & Li, G. (2018). Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams. Organic letters, 20(9), 2595-2598. https://doi.org/10.1021/acs.orglett.8b00786
Zhang, Chunhui, et al. "Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams." Organic letters vol. 20,9 (2018): 2595-2598. doi: https://doi.org/10.1021/acs.orglett.8b00786
Zhang C, Ding Y, Gao Y, Li S, Li G. Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams. Org Lett. 2018 May 04;20(9):2595-2598. doi: 10.1021/acs.orglett.8b00786. Epub 2018 Apr 23. PMID: 29683329.
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Oxidant-Controlled C-sp.

The Journal of organic chemistry

Sharma R, Abdullaha M, Bharate SB.
PMID: 28820259
J Org Chem. 2017 Sep 15;82(18):9786-9793. doi: 10.1021/acs.joc.7b00856. Epub 2017 Aug 29.

Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp

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Sharma R, Abdullaha M, Bharate SB. Oxidant-Controlled C-sp. J Org Chem. 2017;82(18):9786-9793doi: 10.1021/acs.joc.7b00856.
Sharma, R., Abdullaha, M., & Bharate, S. B. (2017). Oxidant-Controlled C-sp. The Journal of organic chemistry, 82(18), 9786-9793. https://doi.org/10.1021/acs.joc.7b00856
Sharma, Rohit, et al. "Oxidant-Controlled C-sp." The Journal of organic chemistry vol. 82,18 (2017): 9786-9793. doi: https://doi.org/10.1021/acs.joc.7b00856
Sharma R, Abdullaha M, Bharate SB. Oxidant-Controlled C-sp. J Org Chem. 2017 Sep 15;82(18):9786-9793. doi: 10.1021/acs.joc.7b00856. Epub 2017 Aug 29. PMID: 28820259.
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Metal-Free Blue Dye Synthesis: Oxidative Coupling of Benzylamines and N,N-Dimethylanilines to Yield 4,4'-Diaminotriarylmethanes in the Presence of Salicylic Acid as a Co-oxidant.

The Journal of organic chemistry

Dong CP, Kodama S, Uematsu A, Nomoto A, Ueshima M, Ogawa A.
PMID: 29092395
J Org Chem. 2017 Dec 01;82(23):12530-12538. doi: 10.1021/acs.joc.7b02296. Epub 2017 Nov 14.

A convenient, novel, and metal-free method for the synthesis of 4,4'-diaminotriarylmethanes (DTMs) is described. This process is based on a one-pot condensation of benzylamines with N,N-dimethylaniline derivatives using 4,6-dihydroxysalicylic acid as a co-oxidant and N-iodosuccinimide as an oxidant. To...

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Dong CP, Kodama S, Uematsu A, et al. Metal-Free Blue Dye Synthesis: Oxidative Coupling of Benzylamines and N,N-Dimethylanilines to Yield 4,4'-Diaminotriarylmethanes in the Presence of Salicylic Acid as a Co-oxidant. J Org Chem. 2017;82(23):12530-12538doi: 10.1021/acs.joc.7b02296.
Dong, C. P., Kodama, S., Uematsu, A., Nomoto, A., Ueshima, M., & Ogawa, A. (2017). Metal-Free Blue Dye Synthesis: Oxidative Coupling of Benzylamines and N,N-Dimethylanilines to Yield 4,4'-Diaminotriarylmethanes in the Presence of Salicylic Acid as a Co-oxidant. The Journal of organic chemistry, 82(23), 12530-12538. https://doi.org/10.1021/acs.joc.7b02296
Dong, Chun-Ping, et al. "Metal-Free Blue Dye Synthesis: Oxidative Coupling of Benzylamines and N,N-Dimethylanilines to Yield 4,4'-Diaminotriarylmethanes in the Presence of Salicylic Acid as a Co-oxidant." The Journal of organic chemistry vol. 82,23 (2017): 12530-12538. doi: https://doi.org/10.1021/acs.joc.7b02296
Dong CP, Kodama S, Uematsu A, Nomoto A, Ueshima M, Ogawa A. Metal-Free Blue Dye Synthesis: Oxidative Coupling of Benzylamines and N,N-Dimethylanilines to Yield 4,4'-Diaminotriarylmethanes in the Presence of Salicylic Acid as a Co-oxidant. J Org Chem. 2017 Dec 01;82(23):12530-12538. doi: 10.1021/acs.joc.7b02296. Epub 2017 Nov 14. PMID: 29092395.
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Electrochemical Dehydrogenative Imidation of N-Methyl-Substituted Benzylamines with Phthalimides for the Direct Synthesis of Phthalimide-Protected gem-Diamines.

Organic letters

Lian F, Sun C, Xu K, Zeng C.
PMID: 30570263
Org Lett. 2019 Jan 04;21(1):156-159. doi: 10.1021/acs.orglett.8b03624. Epub 2018 Dec 20.

A general and green electrochemical dehydrogenative method for the imidation of N-methyl benzylamines with phthalimides with excellent regioselectivities is reported for the first time. This operationally simple method offers a valuable tool to obtain structurally diverse phthalimide-protected gem-diamines.

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Lian F, Sun C, Xu K, et al. Electrochemical Dehydrogenative Imidation of N-Methyl-Substituted Benzylamines with Phthalimides for the Direct Synthesis of Phthalimide-Protected gem-Diamines. Org Lett. 2018;21(1):156-159doi: 10.1021/acs.orglett.8b03624.
Lian, F., Sun, C., Xu, K., & Zeng, C. (2019). Electrochemical Dehydrogenative Imidation of N-Methyl-Substituted Benzylamines with Phthalimides for the Direct Synthesis of Phthalimide-Protected gem-Diamines. Organic letters, 21(1), 156-159. https://doi.org/10.1021/acs.orglett.8b03624
Lian, Fei, et al. "Electrochemical Dehydrogenative Imidation of N-Methyl-Substituted Benzylamines with Phthalimides for the Direct Synthesis of Phthalimide-Protected gem-Diamines." Organic letters vol. 21,1 (2019): 156-159. doi: https://doi.org/10.1021/acs.orglett.8b03624
Lian F, Sun C, Xu K, Zeng C. Electrochemical Dehydrogenative Imidation of N-Methyl-Substituted Benzylamines with Phthalimides for the Direct Synthesis of Phthalimide-Protected gem-Diamines. Org Lett. 2019 Jan 04;21(1):156-159. doi: 10.1021/acs.orglett.8b03624. Epub 2018 Dec 20. PMID: 30570263.
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Showing 1 to 12 of 138 entries