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Developing lithium chemistry of 1,2-dihydropyridines: from kinetic intermediates to isolable characterized compounds.

Chemistry (Weinheim an der Bergstrasse, Germany)

Armstrong DR, Harris CM, Kennedy AR, Liggat JJ, McLellan R, Mulvey RE, Urquhart MD, Robertson SD.
PMID: 26333094
Chemistry. 2015 Oct 05;21(41):14410-20. doi: 10.1002/chem.201501880. Epub 2015 Aug 31.

Generally considered kinetic intermediates in addition reactions of alkyllithiums to pyridine, 1-lithio-2-alkyl-1,2-dihydropyridines have been rarely isolated or characterized. This study develops their "isolated" chemistry. By a unique stoichiometric (that is, 1:1, alkyllithium/pyridine ratios) synthetic approach using tridentate donors we...

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Armstrong DR, Harris CM, Kennedy AR, et al. Developing lithium chemistry of 1,2-dihydropyridines: from kinetic intermediates to isolable characterized compounds. Chemistry. 2015;21(41):14410-20doi: 10.1002/chem.201501880.
Armstrong, D. R., Harris, C. M., Kennedy, A. R., Liggat, J. J., McLellan, R., Mulvey, R. E., Urquhart, M. D., & Robertson, S. D. (2015). Developing lithium chemistry of 1,2-dihydropyridines: from kinetic intermediates to isolable characterized compounds. Chemistry (Weinheim an der Bergstrasse, Germany), 21(41), 14410-20. https://doi.org/10.1002/chem.201501880
Armstrong, David R, et al. "Developing lithium chemistry of 1,2-dihydropyridines: from kinetic intermediates to isolable characterized compounds." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,41 (2015): 14410-20. doi: https://doi.org/10.1002/chem.201501880
Armstrong DR, Harris CM, Kennedy AR, Liggat JJ, McLellan R, Mulvey RE, Urquhart MD, Robertson SD. Developing lithium chemistry of 1,2-dihydropyridines: from kinetic intermediates to isolable characterized compounds. Chemistry. 2015 Oct 05;21(41):14410-20. doi: 10.1002/chem.201501880. Epub 2015 Aug 31. PMID: 26333094.
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One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines.

Organic & biomolecular chemistry

Rao HS, Parthiban A.
PMID: 25007896
Org Biomol Chem. 2014 Aug 28;12(32):6223-38. doi: 10.1039/c4ob00628c.

We have described the simple, convenient and high yielding one-pot synthesis of a library of highly functionalized hexa-substituted 1,4-dihydropyridines (1,4-DHPs) by 2-aminopyridine catalysed pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes. This domino transformation involves formation of dihydropyridine ring by...

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Rao HS, Parthiban A. One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines. Org Biomol Chem. 2014;12(32):6223-38doi: 10.1039/c4ob00628c.
Rao, H. S., & Parthiban, A. (2014). One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines. Organic & biomolecular chemistry, 12(32), 6223-38. https://doi.org/10.1039/c4ob00628c
Rao, H Surya Prakash, and Parthiban, A. "One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines." Organic & biomolecular chemistry vol. 12,32 (2014): 6223-38. doi: https://doi.org/10.1039/c4ob00628c
Rao HS, Parthiban A. One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines. Org Biomol Chem. 2014 Aug 28;12(32):6223-38. doi: 10.1039/c4ob00628c. PMID: 25007896.
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Catalytic Reduction of CO2 by Renewable Organohydrides.

The journal of physical chemistry letters

Lim CH, Holder AM, Hynes JT, Musgrave CB.
PMID: 26722706
J Phys Chem Lett. 2015 Dec 17;6(24):5078-92. doi: 10.1021/acs.jpclett.5b01827. Epub 2015 Dec 10.

Dihydropyridines are renewable organohydride reducing agents for the catalytic reduction of CO2 to MeOH. Here we discuss various aspects of this important reduction. A centerpiece, which illustrates various general principles, is our theoretical catalytic mechanism for CO2 reduction by...

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Lim CH, Holder AM, Hynes JT, et al. Catalytic Reduction of CO2 by Renewable Organohydrides. J Phys Chem Lett. 2015;6(24):5078-92doi: 10.1021/acs.jpclett.5b01827.
Lim, C. H., Holder, A. M., Hynes, J. T., & Musgrave, C. B. (2015). Catalytic Reduction of CO2 by Renewable Organohydrides. The journal of physical chemistry letters, 6(24), 5078-92. https://doi.org/10.1021/acs.jpclett.5b01827
Lim, Chern-Hooi, et al. "Catalytic Reduction of CO2 by Renewable Organohydrides." The journal of physical chemistry letters vol. 6,24 (2015): 5078-92. doi: https://doi.org/10.1021/acs.jpclett.5b01827
Lim CH, Holder AM, Hynes JT, Musgrave CB. Catalytic Reduction of CO2 by Renewable Organohydrides. J Phys Chem Lett. 2015 Dec 17;6(24):5078-92. doi: 10.1021/acs.jpclett.5b01827. Epub 2015 Dec 10. PMID: 26722706.
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The Novel Development of an Experimental Model of Dihydropyridine Calcium Channel Blocker Poisoning using Intravenous Amlodipine.

International journal of cardiovascular research

Jang D, Donovan S, Bania T, Nelson L, Hoffman R, Chu J.
PMID: 24416727
Int J Cardiovasc Res. 2013 Mar 29;2(2):1000121.

BACKGROUND: Cardiovascular drug poisoning remains a leading cause of fatality. Within this class, calcium channel blockers (CCBs) account for the majority of deaths. CCBs are typically categorized as dihydropyridines (i.e. amlodipine or nifedipine) versus the non-dihydropyridine (i.e. verapamil and...

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Jang D, Donovan S, Bania T, et al. The Novel Development of an Experimental Model of Dihydropyridine Calcium Channel Blocker Poisoning using Intravenous Amlodipine. Int J Cardiovasc Res. 2013;2(2):1000121
Jang, D., Donovan, S., Bania, T., Nelson, L., Hoffman, R., & Chu, J. (2013). The Novel Development of an Experimental Model of Dihydropyridine Calcium Channel Blocker Poisoning using Intravenous Amlodipine. International journal of cardiovascular research, 2(2), 1000121.
Jang, David, et al. "The Novel Development of an Experimental Model of Dihydropyridine Calcium Channel Blocker Poisoning using Intravenous Amlodipine." International journal of cardiovascular research vol. 2,2 (2013): 1000121.
Jang D, Donovan S, Bania T, Nelson L, Hoffman R, Chu J. The Novel Development of an Experimental Model of Dihydropyridine Calcium Channel Blocker Poisoning using Intravenous Amlodipine. Int J Cardiovasc Res. 2013 Mar 29;2(2):1000121. PMID: 24416727; PMCID: PMC3886834.
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Synthesis of novel 1,8-acridinediones derivatives: Investigation of MDR reversibility on breast cancer cell lines T47D and tamoxifen-resistant T47D.

Research in pharmaceutical sciences

Moallem SA, Dehghani N, Mehri S, Shahsavand Sh, Alibolandi M, Hadizadeh F.
PMID: 26600848
Res Pharm Sci. 2015 May-Jun;10(3):214-21.

Multi drug resistance (MDR) is a serious obstacle in the management of breast cancer. Therefore, overcoming MDR using novel anticancer agents is a top priority for medicinal chemists. It was found that dihydropyridines lacking calcium antagonistic activity (e.g acridinediones)...

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Moallem SA, Dehghani N, Mehri S, et al. Synthesis of novel 1,8-acridinediones derivatives: Investigation of MDR reversibility on breast cancer cell lines T47D and tamoxifen-resistant T47D. Res Pharm Sci. 2015;10(3):214-21
Moallem, S. A., Dehghani, N., Mehri, S., Shahsavand, S. h., Alibolandi, M., & Hadizadeh, F. (2015). Synthesis of novel 1,8-acridinediones derivatives: Investigation of MDR reversibility on breast cancer cell lines T47D and tamoxifen-resistant T47D. Research in pharmaceutical sciences, 10(3), 214-21.
Moallem, S A, et al. "Synthesis of novel 1,8-acridinediones derivatives: Investigation of MDR reversibility on breast cancer cell lines T47D and tamoxifen-resistant T47D." Research in pharmaceutical sciences vol. 10,3 (2015): 214-21.
Moallem SA, Dehghani N, Mehri S, Shahsavand Sh, Alibolandi M, Hadizadeh F. Synthesis of novel 1,8-acridinediones derivatives: Investigation of MDR reversibility on breast cancer cell lines T47D and tamoxifen-resistant T47D. Res Pharm Sci. 2015 May-Jun;10(3):214-21. PMID: 26600848; PMCID: PMC4621628.
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New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks.

Journal of the American Chemical Society

Chen S, Bacauanu V, Knecht T, Mercado BQ, Bergman RG, Ellman JA.
PMID: 27642766
J Am Chem Soc. 2016 Sep 28;138(38):12664-70. doi: 10.1021/jacs.6b08355. Epub 2016 Sep 19.

Multisubstituted tropanes and indolizidines have been prepared with high regio- and stereoselectivity by the [3+2] cycloaddition of unstabilized azomethine ylides generated from readily prepared trimethylsilyl-substituted 1,2-dihydropyridines via protonation or alkylation followed by desilylation. Starting from 1,2-dihydropyridines bearing a ring...

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Chen S, Bacauanu V, Knecht T, et al. New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks. J Am Chem Soc. 2016;138(38):12664-70doi: 10.1021/jacs.6b08355.
Chen, S., Bacauanu, V., Knecht, T., Mercado, B. Q., Bergman, R. G., & Ellman, J. A. (2016). New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks. Journal of the American Chemical Society, 138(38), 12664-70. https://doi.org/10.1021/jacs.6b08355
Chen, Shuming, et al. "New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks." Journal of the American Chemical Society vol. 138,38 (2016): 12664-70. doi: https://doi.org/10.1021/jacs.6b08355
Chen S, Bacauanu V, Knecht T, Mercado BQ, Bergman RG, Ellman JA. New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks. J Am Chem Soc. 2016 Sep 28;138(38):12664-70. doi: 10.1021/jacs.6b08355. Epub 2016 Sep 19. PMID: 27642766; PMCID: PMC5066814.
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Enantioselective .

Chemical science

Flanigan DM, Rovis T.
PMID: 28989683
Chem Sci. 2017 Sep 01;8(9):6566-6569. doi: 10.1039/c7sc02648j. Epub 2017 Aug 03.

NHC-catalyzed nucleophilic dearomatization of alkyl pyridiniums has been achieved to generate 1,4-dihydropyridines with high enantioselectivity. This is a rare example of catalytic, asymmetric addition of a nucleophile to the activated pyridinium that prefers C-4 functionalization leading to the 1,4-dihydropyridine...

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Flanigan DM, Rovis T. Enantioselective . Chem Sci. 2017;8(9):6566-6569doi: 10.1039/c7sc02648j.
Flanigan, D. M., & Rovis, T. (2017). Enantioselective . Chemical science, 8(9), 6566-6569. https://doi.org/10.1039/c7sc02648j
Flanigan, Darrin M, and Rovis, Tomislav. "Enantioselective ." Chemical science vol. 8,9 (2017): 6566-6569. doi: https://doi.org/10.1039/c7sc02648j
Flanigan DM, Rovis T. Enantioselective . Chem Sci. 2017 Sep 01;8(9):6566-6569. doi: 10.1039/c7sc02648j. Epub 2017 Aug 03. PMID: 28989683; PMCID: PMC5627355.
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Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines.

Angewandte Chemie (International ed. in English)

Wang SG, Xia ZL, Xu RQ, Liu XJ, Zheng C, You SL.
PMID: 28466512
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7440-7443. doi: 10.1002/anie.201703178. Epub 2017 May 23.

A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet-Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent...

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Wang SG, Xia ZL, Xu RQ, et al. Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angew Chem Int Ed Engl. 2017;56(26):7440-7443doi: 10.1002/anie.201703178.
Wang, S. G., Xia, Z. L., Xu, R. Q., Liu, X. J., Zheng, C., & You, S. L. (2017). Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angewandte Chemie (International ed. in English), 56(26), 7440-7443. https://doi.org/10.1002/anie.201703178
Wang, Shou-Guo, et al. "Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines." Angewandte Chemie (International ed. in English) vol. 56,26 (2017): 7440-7443. doi: https://doi.org/10.1002/anie.201703178
Wang SG, Xia ZL, Xu RQ, Liu XJ, Zheng C, You SL. Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7440-7443. doi: 10.1002/anie.201703178. Epub 2017 May 23. PMID: 28466512.
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The First Functionalized 6,12-Diazatetrakishomocubanes.

Angewandte Chemie (International ed. in English)

Hilgeroth A, Baumeister U.
PMID: 10671263
Angew Chem Int Ed Engl. 2000 Feb;39(3):576-578. doi: 10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g.

The photodimerization of asymmetric 4-aryl-1,4-dihydropyridines results, totally unexpectedly, in the new 6,12-diazatetrakishomocubanes 1. This is in contrast to the previously observed [2+2] photocycloaddition reactions of symmetrical 4-aryl-1,4-dihydropyridines

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Hilgeroth A, Baumeister U. The First Functionalized 6,12-Diazatetrakishomocubanes. Angew Chem Int Ed Engl. 2000;39(3):576-578doi: 10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g.
Hilgeroth, A., & Baumeister, U. (2000). The First Functionalized 6,12-Diazatetrakishomocubanes. Angewandte Chemie (International ed. in English), 39(3), 576-578. https://doi.org/10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g
Hilgeroth, and Baumeister. "The First Functionalized 6,12-Diazatetrakishomocubanes." Angewandte Chemie (International ed. in English) vol. 39,3 (2000): 576-578. doi: https://doi.org/10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g
Hilgeroth A, Baumeister U. The First Functionalized 6,12-Diazatetrakishomocubanes. Angew Chem Int Ed Engl. 2000 Feb;39(3):576-578. doi: 10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g. PMID: 10671263.
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Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility.

Chemical communications (Cambridge, England)

Cave GW, Raston CL, Scott JL.
PMID: 12240095
Chem Commun (Camb). 2001 Nov 07;(21):2159-69.

A paradigm shift away from using solvents in organic synthesis as solventless reactions can lead to improved outcomes, and more benign synthetic procedures, in for example aldol condensation reactions, sequential aldol and Michael addition reactions en route to Kröhnke...

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Cave GW, Raston CL, Scott JL. Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chem Commun (Camb). 2001;(21):2159-69
Cave, G. W., Raston, C. L., & Scott, J. L. (2001). Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chemical communications (Cambridge, England), (21), 2159-69.
Cave, G W, et al. "Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility." Chemical communications (Cambridge, England) vol. ,21 (2001): 2159-69.
Cave GW, Raston CL, Scott JL. Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chem Commun (Camb). 2001 Nov 07;(21):2159-69. PMID: 12240095.
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Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid.

Organic letters

Nakamichi N, Kawashita Y, Hayashi M.
PMID: 12599501
Org Lett. 2002 Oct 31;4(22):3955-7. doi: 10.1021/ol0268135.

[formula: see text] 1,3,5-Trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines were converted to the corresponding pyrazoles and pyridines effectively by the treatment of a catalytic amount of Pd/C in acetic acid.

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Nakamichi N, Kawashita Y, Hayashi M. Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid. Org Lett. 2002;4(22):3955-7doi: 10.1021/ol0268135.
Nakamichi, N., Kawashita, Y., & Hayashi, M. (2002). Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid. Organic letters, 4(22), 3955-7. https://doi.org/10.1021/ol0268135
Nakamichi, Natsuki, et al. "Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid." Organic letters vol. 4,22 (2002): 3955-7. doi: https://doi.org/10.1021/ol0268135
Nakamichi N, Kawashita Y, Hayashi M. Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid. Org Lett. 2002 Oct 31;4(22):3955-7. doi: 10.1021/ol0268135. PMID: 12599501.
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Electrophilic Oxidative Additions upon 1,4-Dihydropyridines.

The Journal of organic chemistry

Lavilla R, Coll O, Kumar R, Bosch J.
PMID: 11672145
J Org Chem. 1998 Apr 17;63(8):2728-2730. doi: 10.1021/jo971947v.

No abstract available.

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Lavilla R, Coll O, Kumar R, et al. Electrophilic Oxidative Additions upon 1,4-Dihydropyridines. J Org Chem. 1998;63(8):2728-2730doi: 10.1021/jo971947v.
Lavilla, R., Coll, O., Kumar, R., & Bosch, J. (1998). Electrophilic Oxidative Additions upon 1,4-Dihydropyridines. The Journal of organic chemistry, 63(8), 2728-2730. https://doi.org/10.1021/jo971947v
Lavilla, Rodolfo, et al. "Electrophilic Oxidative Additions upon 1,4-Dihydropyridines." The Journal of organic chemistry vol. 63,8 (1998): 2728-2730. doi: https://doi.org/10.1021/jo971947v
Lavilla R, Coll O, Kumar R, Bosch J. Electrophilic Oxidative Additions upon 1,4-Dihydropyridines. J Org Chem. 1998 Apr 17;63(8):2728-2730. doi: 10.1021/jo971947v. PMID: 11672145.
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Showing 1 to 12 of 205 entries