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Chains, necklaces and weaving chain-link grids from self-assembly reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Alvariño C, Simond D, Lorente PM, Besnard C, Williams AF.
PMID: 25950771
Chemistry. 2015 Jun 08;21(24):8851-8. doi: 10.1002/chem.201501091. Epub 2015 May 07.

Assembly of two ditopic units, a phenanthroline substituted by 4-ethynyl pyridines at the 2-and 9-positions and a dimetallic paddlewheel, gives a linear chain polymer rather than a closed cyclic species, which would appear equally possible. The chain may be...

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Alvariño C, Simond D, Lorente PM, et al. Chains, necklaces and weaving chain-link grids from self-assembly reactions. Chemistry. 2015;21(24):8851-8doi: 10.1002/chem.201501091.
Alvariño, C., Simond, D., Lorente, P. M., Besnard, C., & Williams, A. F. (2015). Chains, necklaces and weaving chain-link grids from self-assembly reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 21(24), 8851-8. https://doi.org/10.1002/chem.201501091
Alvariño, Cristina, et al. "Chains, necklaces and weaving chain-link grids from self-assembly reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,24 (2015): 8851-8. doi: https://doi.org/10.1002/chem.201501091
Alvariño C, Simond D, Lorente PM, Besnard C, Williams AF. Chains, necklaces and weaving chain-link grids from self-assembly reactions. Chemistry. 2015 Jun 08;21(24):8851-8. doi: 10.1002/chem.201501091. Epub 2015 May 07. PMID: 25950771.
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An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides.

Organic & biomolecular chemistry

Mu B, Wu Y, Li J, Zou D, Chang J, Wu Y.
PMID: 26566049
Org Biomol Chem. 2016 Jan 07;14(1):246-50. doi: 10.1039/c5ob02112j.

An efficient and practical protocol for palladium-catalyzed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids with aryl chlorides has been developed. Note that the reaction could proceed smoothly without an additive in aqueous medium under an ambient atmosphere, and the addition of...

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Mu B, Wu Y, Li J, et al. An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides. Org Biomol Chem. 2016;14(1):246-50doi: 10.1039/c5ob02112j.
Mu, B., Wu, Y., Li, J., Zou, D., Chang, J., & Wu, Y. (2016). An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides. Organic & biomolecular chemistry, 14(1), 246-50. https://doi.org/10.1039/c5ob02112j
Mu, Bing, et al. "An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides." Organic & biomolecular chemistry vol. 14,1 (2016): 246-50. doi: https://doi.org/10.1039/c5ob02112j
Mu B, Wu Y, Li J, Zou D, Chang J, Wu Y. An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides. Org Biomol Chem. 2016 Jan 07;14(1):246-50. doi: 10.1039/c5ob02112j. PMID: 26566049.
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Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions.

Beilstein journal of organic chemistry

Zhang LJ, Wu Q, Sun J, Yan CG.
PMID: 23766799
Beilstein J Org Chem. 2013 May 02;9:846-51. doi: 10.3762/bjoc.9.97. Print 2013.

In the presence of triethylamine as catalyst, the one-pot four-component reactions of arylamines, methyl propiolate, isatin and malononitrile afforded the functionalized spiro[indoline-3,4'-pyridine] derivatives in good yields. Similar reactions with ethyl cyanoacetate successfully afforded the functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] as...

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Zhang LJ, Wu Q, Sun J, et al. Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions. Beilstein J Org Chem. 2013;9:846-51doi: 10.3762/bjoc.9.97.
Zhang, L. J., Wu, Q., Sun, J., & Yan, C. G. (2013). Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions. Beilstein journal of organic chemistry, 9846-51. https://doi.org/10.3762/bjoc.9.97
Zhang, Li-Juan, et al. "Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions." Beilstein journal of organic chemistry vol. 9 (2013): 846-51. doi: https://doi.org/10.3762/bjoc.9.97
Zhang LJ, Wu Q, Sun J, Yan CG. Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions. Beilstein J Org Chem. 2013 May 02;9:846-51. doi: 10.3762/bjoc.9.97. Print 2013. PMID: 23766799; PMCID: PMC3678513.
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Ruthenium complexes of tripodal ligands with pyridine and triazole arms: subtle tuning of thermal, electrochemical, and photochemical reactivity.

Chemistry (Weinheim an der Bergstrasse, Germany)

Weisser F, Hohloch S, Plebst S, Schweinfurth D, Sarkar B.
PMID: 24403171
Chemistry. 2014 Jan 13;20(3):781-93. doi: 10.1002/chem.201303640. Epub 2014 Jan 08.

Electrochemical and photochemical bond-activation steps are important for a variety of chemical transformations. We present here four new complexes, [Ru(L(n) )(dmso)(Cl)]PF6 (1-4), where L(n) is a tripodal amine ligand with 4-n pyridylmethyl arms and n-1 triazolylmethyl arms. Structural comparisons...

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Weisser F, Hohloch S, Plebst S, et al. Ruthenium complexes of tripodal ligands with pyridine and triazole arms: subtle tuning of thermal, electrochemical, and photochemical reactivity. Chemistry. 2014;20(3):781-93doi: 10.1002/chem.201303640.
Weisser, F., Hohloch, S., Plebst, S., Schweinfurth, D., & Sarkar, B. (2014). Ruthenium complexes of tripodal ligands with pyridine and triazole arms: subtle tuning of thermal, electrochemical, and photochemical reactivity. Chemistry (Weinheim an der Bergstrasse, Germany), 20(3), 781-93. https://doi.org/10.1002/chem.201303640
Weisser, Fritz, et al. "Ruthenium complexes of tripodal ligands with pyridine and triazole arms: subtle tuning of thermal, electrochemical, and photochemical reactivity." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,3 (2014): 781-93. doi: https://doi.org/10.1002/chem.201303640
Weisser F, Hohloch S, Plebst S, Schweinfurth D, Sarkar B. Ruthenium complexes of tripodal ligands with pyridine and triazole arms: subtle tuning of thermal, electrochemical, and photochemical reactivity. Chemistry. 2014 Jan 13;20(3):781-93. doi: 10.1002/chem.201303640. Epub 2014 Jan 08. PMID: 24403171.
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Discovery of Novel Imidazo[4,5-b]pyridines as Potent and Selective Inhibitors of Phosphodiesterase 10A (PDE10A).

ACS medicinal chemistry letters

Hu E, Andrews K, Chmait S, Zhao X, Davis C, Miller S, Hill Della Puppa G, Dovlatyan M, Chen H, Lester-Zeiner D, Able J, Biorn C, Ma J, Shi J, Treanor J, Allen JR.
PMID: 24944747
ACS Med Chem Lett. 2014 Mar 28;5(6):700-5. doi: 10.1021/ml5000993. eCollection 2014 Jun 12.

We report the discovery of novel imidazo[4,5-b]pyridines as potent and selective inhibitors of PDE10A. The investigation began with our recently disclosed ketobenzimidazole 1, which exhibited single digit nanomolar PDE10A activity but poor oral bioavailability. To improve oral bioavailability, we...

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Hu E, Andrews K, Chmait S, et al. Discovery of Novel Imidazo[4,5-b]pyridines as Potent and Selective Inhibitors of Phosphodiesterase 10A (PDE10A). ACS Med Chem Lett. 2014;5(6):700-5doi: 10.1021/ml5000993.
Hu, E., Andrews, K., Chmait, S., Zhao, X., Davis, C., Miller, S., Hill Della Puppa, G., Dovlatyan, M., Chen, H., Lester-Zeiner, D., Able, J., Biorn, C., Ma, J., Shi, J., Treanor, J., & Allen, J. R. (2014). Discovery of Novel Imidazo[4,5-b]pyridines as Potent and Selective Inhibitors of Phosphodiesterase 10A (PDE10A). ACS medicinal chemistry letters, 5(6), 700-5. https://doi.org/10.1021/ml5000993
Hu, Essa, et al. "Discovery of Novel Imidazo[4,5-b]pyridines as Potent and Selective Inhibitors of Phosphodiesterase 10A (PDE10A)." ACS medicinal chemistry letters vol. 5,6 (2014): 700-5. doi: https://doi.org/10.1021/ml5000993
Hu E, Andrews K, Chmait S, Zhao X, Davis C, Miller S, Hill Della Puppa G, Dovlatyan M, Chen H, Lester-Zeiner D, Able J, Biorn C, Ma J, Shi J, Treanor J, Allen JR. Discovery of Novel Imidazo[4,5-b]pyridines as Potent and Selective Inhibitors of Phosphodiesterase 10A (PDE10A). ACS Med Chem Lett. 2014 Mar 28;5(6):700-5. doi: 10.1021/ml5000993. eCollection 2014 Jun 12. PMID: 24944747; PMCID: PMC4060924.
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Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction.

The Journal of organic chemistry

Wan JP, Lin Y, Huang Q, Liu Y.
PMID: 25003698
J Org Chem. 2014 Aug 01;79(15):7232-8. doi: 10.1021/jo501292q. Epub 2014 Jul 15.

The three-component reactions of enals, electron-deficient alkynes, and hydroxyl-functionalized primary amines for the highly diastereoselective construction of dihydro-3H-benzo[4,5]oxazolo[3,2-a]pyridines, hexahydropyrido[2,1-b][1,3]oxazines, and tetrahydro-2H-oxazolo[3,2-a]pyridines have been achieved. Domino formation of one C-C, two C-N, and one C-O bonds are furnished in these...

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Wan JP, Lin Y, Huang Q, et al. Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction. J Org Chem. 2014;79(15):7232-8doi: 10.1021/jo501292q.
Wan, J. P., Lin, Y., Huang, Q., & Liu, Y. (2014). Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction. The Journal of organic chemistry, 79(15), 7232-8. https://doi.org/10.1021/jo501292q
Wan, Jie-Ping, et al. "Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction." The Journal of organic chemistry vol. 79,15 (2014): 7232-8. doi: https://doi.org/10.1021/jo501292q
Wan JP, Lin Y, Huang Q, Liu Y. Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction. J Org Chem. 2014 Aug 01;79(15):7232-8. doi: 10.1021/jo501292q. Epub 2014 Jul 15. PMID: 25003698.
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Regioselective Pd-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Isoxazolinones.

The Journal of organic chemistry

Rieckhoff S, Hellmuth T, Peters R.
PMID: 26101943
J Org Chem. 2015 Jul 02;80(13):6822-30. doi: 10.1021/acs.joc.5b01065. Epub 2015 Jun 23.

Substituted pyridines are prevalent heterocycles of fundamental importance. Their efficient regioselective preparation is often still a challenge despite a large number of reported synthetic methodologies. In this letter we report an operationally simple approach that makes use of readily...

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Rieckhoff S, Hellmuth T, Peters R. Regioselective Pd-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Isoxazolinones. J Org Chem. 2015;80(13):6822-30doi: 10.1021/acs.joc.5b01065.
Rieckhoff, S., Hellmuth, T., & Peters, R. (2015). Regioselective Pd-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Isoxazolinones. The Journal of organic chemistry, 80(13), 6822-30. https://doi.org/10.1021/acs.joc.5b01065
Rieckhoff, Stefan, et al. "Regioselective Pd-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Isoxazolinones." The Journal of organic chemistry vol. 80,13 (2015): 6822-30. doi: https://doi.org/10.1021/acs.joc.5b01065
Rieckhoff S, Hellmuth T, Peters R. Regioselective Pd-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Isoxazolinones. J Org Chem. 2015 Jul 02;80(13):6822-30. doi: 10.1021/acs.joc.5b01065. Epub 2015 Jun 23. PMID: 26101943.
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Transition-metal-catalyzed asymmetric allylic dearomatization reactions.

Accounts of chemical research

Zhuo CX, Zheng C, You SL.
PMID: 24940612
Acc Chem Res. 2014 Aug 19;47(8):2558-73. doi: 10.1021/ar500167f. Epub 2014 Jun 18.

Dearomatization reactions serve as powerful methods for the synthesis of highly functionalized, three-dimensional structures starting with simple planar aromatic compounds. Among processes of this type, catalytic asymmetric dearomatization (CADA) reactions are attractive owing to the large number of aromatic...

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Zhuo CX, Zheng C, You SL. Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Acc Chem Res. 2014;47(8):2558-73doi: 10.1021/ar500167f.
Zhuo, C. X., Zheng, C., & You, S. L. (2014). Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Accounts of chemical research, 47(8), 2558-73. https://doi.org/10.1021/ar500167f
Zhuo, Chun-Xiang, et al. "Transition-metal-catalyzed asymmetric allylic dearomatization reactions." Accounts of chemical research vol. 47,8 (2014): 2558-73. doi: https://doi.org/10.1021/ar500167f
Zhuo CX, Zheng C, You SL. Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Acc Chem Res. 2014 Aug 19;47(8):2558-73. doi: 10.1021/ar500167f. Epub 2014 Jun 18. PMID: 24940612.
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Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles.

Organic & biomolecular chemistry

Mishra S, Mondal P, Ghosh M, Mondal S, Hajra A.
PMID: 26676998
Org Biomol Chem. 2016 Jan 28;14(4):1432-6. doi: 10.1039/c5ob02363g. Epub 2015 Dec 17.

A regioselective copper-catalyzed ethoxycarbonyl-difluoromethylation of imidazo[1,2-a]pyridines has been developed through sp(2) C-H bond functionalization with BrCF2CO2Et under ambient air. A series of ethoxycarbonyldifluoromethylated imidazo[1,2-a]pyridines with broad functionalities have been synthesized. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

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Mishra S, Mondal P, Ghosh M, et al. Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles. Org Biomol Chem. 2015;14(4):1432-6doi: 10.1039/c5ob02363g.
Mishra, S., Mondal, P., Ghosh, M., Mondal, S., & Hajra, A. (2016). Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles. Organic & biomolecular chemistry, 14(4), 1432-6. https://doi.org/10.1039/c5ob02363g
Mishra, Subhajit, et al. "Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles." Organic & biomolecular chemistry vol. 14,4 (2016): 1432-6. doi: https://doi.org/10.1039/c5ob02363g
Mishra S, Mondal P, Ghosh M, Mondal S, Hajra A. Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles. Org Biomol Chem. 2016 Jan 28;14(4):1432-6. doi: 10.1039/c5ob02363g. Epub 2015 Dec 17. PMID: 26676998.
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Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts.

Chemistry (Weinheim an der Bergstrasse, Germany)

Renom-Carrasco M, Gajewski P, Pignataro L, de Vries JG, Piarulli U, Gennari C, Lefort L.
PMID: 27140832
Chemistry. 2016 Jul 04;22(28):9528-32. doi: 10.1002/chem.201601501. Epub 2016 Jun 03.

The use of an equivalent amount of an organic base leads to high enantiomeric excess in the asymmetric hydrogenation of N-benzylated 3-substituted pyridinium salts into the corresponding piperidines. Indeed, in the presence of Et3 N, a Rh-JosiPhos catalyst reduced...

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Renom-Carrasco M, Gajewski P, Pignataro L, et al. Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry. 2016;22(28):9528-32doi: 10.1002/chem.201601501.
Renom-Carrasco, M., Gajewski, P., Pignataro, L., de Vries, J. G., Piarulli, U., Gennari, C., & Lefort, L. (2016). Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry (Weinheim an der Bergstrasse, Germany), 22(28), 9528-32. https://doi.org/10.1002/chem.201601501
Renom-Carrasco, Marc, et al. "Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,28 (2016): 9528-32. doi: https://doi.org/10.1002/chem.201601501
Renom-Carrasco M, Gajewski P, Pignataro L, de Vries JG, Piarulli U, Gennari C, Lefort L. Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry. 2016 Jul 04;22(28):9528-32. doi: 10.1002/chem.201601501. Epub 2016 Jun 03. PMID: 27140832.
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Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles.

The Journal of organic chemistry

Zhang J, Lu X, Li T, Wang S, Zhong G.
PMID: 28429945
J Org Chem. 2017 May 19;82(10):5222-5229. doi: 10.1021/acs.joc.7b00480. Epub 2017 Apr 27.

A catalytic oxidative cyclization of 2-aminopyridines or 2-aminobenzothiazole with 2-phenoxyacetophenones (a kind of lignin platform compound) was developed, efficiently providing valuable 3-phenoxy imidazo[1,2-a]pyridines or 3-phenoxy benzo[d]imidazo[2,1-b]thiazoles. The reaction was realized under oxygen by simply using inexpensive CuI as the...

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Zhang J, Lu X, Li T, et al. Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. J Org Chem. 2017;82(10):5222-5229doi: 10.1021/acs.joc.7b00480.
Zhang, J., Lu, X., Li, T., Wang, S., & Zhong, G. (2017). Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. The Journal of organic chemistry, 82(10), 5222-5229. https://doi.org/10.1021/acs.joc.7b00480
Zhang, Jian, et al. "Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles." The Journal of organic chemistry vol. 82,10 (2017): 5222-5229. doi: https://doi.org/10.1021/acs.joc.7b00480
Zhang J, Lu X, Li T, Wang S, Zhong G. Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. J Org Chem. 2017 May 19;82(10):5222-5229. doi: 10.1021/acs.joc.7b00480. Epub 2017 Apr 27. PMID: 28429945.
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Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines.

Angewandte Chemie (International ed. in English)

Tan WW, Ong YJ, Yoshikai N.
PMID: 28524343
Angew Chem Int Ed Engl. 2017 Jul 03;56(28):8240-8244. doi: 10.1002/anie.201704378. Epub 2017 Jun 09.

A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a...

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Tan WW, Ong YJ, Yoshikai N. Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines. Angew Chem Int Ed Engl. 2017;56(28):8240-8244doi: 10.1002/anie.201704378.
Tan, W. W., Ong, Y. J., & Yoshikai, N. (2017). Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines. Angewandte Chemie (International ed. in English), 56(28), 8240-8244. https://doi.org/10.1002/anie.201704378
Tan, Wei Wen, et al. "Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines." Angewandte Chemie (International ed. in English) vol. 56,28 (2017): 8240-8244. doi: https://doi.org/10.1002/anie.201704378
Tan WW, Ong YJ, Yoshikai N. Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines. Angew Chem Int Ed Engl. 2017 Jul 03;56(28):8240-8244. doi: 10.1002/anie.201704378. Epub 2017 Jun 09. PMID: 28524343.
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