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Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines.

Chemical communications (Cambridge, England)

Tayama E, Kobayashi Y, Toma Y.
PMID: 27498628
Chem Commun (Camb). 2016 Aug 18;52(69):10570-3. doi: 10.1039/c6cc04626f.

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines was demonstrated. The scope and limitation, experimental mechanistic studies, and a proposed reaction mechanism were also described.

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Tayama E, Kobayashi Y, Toma Y. Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines. Chem Commun (Camb). 2016;52(69):10570-3doi: 10.1039/c6cc04626f.
Tayama, E., Kobayashi, Y., & Toma, Y. (2016). Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines. Chemical communications (Cambridge, England), 52(69), 10570-3. https://doi.org/10.1039/c6cc04626f
Tayama, Eiji, et al. "Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines." Chemical communications (Cambridge, England) vol. 52,69 (2016): 10570-3. doi: https://doi.org/10.1039/c6cc04626f
Tayama E, Kobayashi Y, Toma Y. Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines. Chem Commun (Camb). 2016 Aug 18;52(69):10570-3. doi: 10.1039/c6cc04626f. PMID: 27498628.
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Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kulchat S, Chaur MN, Lehn JM.
PMID: 28628248
Chemistry. 2017 Aug 16;23(46):11108-11118. doi: 10.1002/chem.201702088. Epub 2017 Jul 26.

The kinetic and thermodynamic selectivities of imine formation have been investigated for several dynamic covalent libraries of aldehydes and amines. Two systems were examined, involving the reaction of different types of primary amino groups (aliphatic amines, alkoxy-amines, hydrazides and...

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Kulchat S, Chaur MN, Lehn JM. Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry. Chemistry. 2017;23(46):11108-11118doi: 10.1002/chem.201702088.
Kulchat, S., Chaur, M. N., & Lehn, J. M. (2017). Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry. Chemistry (Weinheim an der Bergstrasse, Germany), 23(46), 11108-11118. https://doi.org/10.1002/chem.201702088
Kulchat, Sirinan, et al. "Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,46 (2017): 11108-11118. doi: https://doi.org/10.1002/chem.201702088
Kulchat S, Chaur MN, Lehn JM. Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry. Chemistry. 2017 Aug 16;23(46):11108-11118. doi: 10.1002/chem.201702088. Epub 2017 Jul 26. PMID: 28628248.
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Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles.

Organic letters

Schneider Y, Prévost J, Gobin M, Legault CY.
PMID: 24378081
Org Lett. 2014 Jan 17;16(2):596-9. doi: 10.1021/ol403495e. Epub 2013 Dec 30.

Even after more than 50 years since its discovery, the electrophilic potential of diazirines was never truly exploited. This longstanding limitation has been resolved. N-Monosubstituted diaziridines and hydrazones are obtained by nucleophilic additions. They release, under hydrolysis conditions, the...

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Schneider Y, Prévost J, Gobin M, et al. Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Org Lett. 2013;16(2):596-9doi: 10.1021/ol403495e.
Schneider, Y., Prévost, J., Gobin, M., & Legault, C. Y. (2014). Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Organic letters, 16(2), 596-9. https://doi.org/10.1021/ol403495e
Schneider, Yoann, et al. "Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles." Organic letters vol. 16,2 (2014): 596-9. doi: https://doi.org/10.1021/ol403495e
Schneider Y, Prévost J, Gobin M, Legault CY. Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Org Lett. 2014 Jan 17;16(2):596-9. doi: 10.1021/ol403495e. Epub 2013 Dec 30. PMID: 24378081.
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Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation.

The Journal of organic chemistry

Agejas J, Ortega L.
PMID: 26018762
J Org Chem. 2015 Jun 19;80(12):6509-14. doi: 10.1021/acs.joc.5b00796. Epub 2015 Jun 05.

The two-step synthesis of spirocyclic pyrazolone derivatives from simple and commercially available reagents is described. The unusual reaction of 1,3-dicarbonyls with hydrazines and an iodine-mediated oxidative carbon-nitrogen bond formation, joined in a two-step, one-pot reaction, allows the straightforward synthesis...

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Agejas J, Ortega L. Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation. J Org Chem. 2015;80(12):6509-14doi: 10.1021/acs.joc.5b00796.
Agejas, J., & Ortega, L. (2015). Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation. The Journal of organic chemistry, 80(12), 6509-14. https://doi.org/10.1021/acs.joc.5b00796
Agejas, Javier, and Ortega, Laura. "Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation." The Journal of organic chemistry vol. 80,12 (2015): 6509-14. doi: https://doi.org/10.1021/acs.joc.5b00796
Agejas J, Ortega L. Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation. J Org Chem. 2015 Jun 19;80(12):6509-14. doi: 10.1021/acs.joc.5b00796. Epub 2015 Jun 05. PMID: 26018762.
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Irida-β-ketoimines Derived from Hydrazines To Afford Metallapyrazoles or N-N Bond Cleavage: A Missing Metallacycle Disclosed by a Theoretical and Experimental Study.

Inorganic chemistry

Zumeta I, Mendicute-Fierro C, Bustos I, Huertos MA, Rodríguez-Diéguez A, Seco JM, San Sebastian E, Garralda MA.
PMID: 27689907
Inorg Chem. 2016 Oct 17;55(20):10284-10293. doi: 10.1021/acs.inorgchem.6b01550. Epub 2016 Sep 30.

Unprecedented metallapyrazoles [IrH

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Zumeta I, Mendicute-Fierro C, Bustos I, et al. Irida-β-ketoimines Derived from Hydrazines To Afford Metallapyrazoles or N-N Bond Cleavage: A Missing Metallacycle Disclosed by a Theoretical and Experimental Study. Inorg Chem. 2016;55(20):10284-10293doi: 10.1021/acs.inorgchem.6b01550.
Zumeta, I., Mendicute-Fierro, C., Bustos, I., Huertos, M. A., Rodríguez-Diéguez, A., Seco, J. M., San Sebastian, E., & Garralda, M. A. (2016). Irida-β-ketoimines Derived from Hydrazines To Afford Metallapyrazoles or N-N Bond Cleavage: A Missing Metallacycle Disclosed by a Theoretical and Experimental Study. Inorganic chemistry, 55(20), 10284-10293. https://doi.org/10.1021/acs.inorgchem.6b01550
Zumeta, Itziar, et al. "Irida-β-ketoimines Derived from Hydrazines To Afford Metallapyrazoles or N-N Bond Cleavage: A Missing Metallacycle Disclosed by a Theoretical and Experimental Study." Inorganic chemistry vol. 55,20 (2016): 10284-10293. doi: https://doi.org/10.1021/acs.inorgchem.6b01550
Zumeta I, Mendicute-Fierro C, Bustos I, Huertos MA, Rodríguez-Diéguez A, Seco JM, San Sebastian E, Garralda MA. Irida-β-ketoimines Derived from Hydrazines To Afford Metallapyrazoles or N-N Bond Cleavage: A Missing Metallacycle Disclosed by a Theoretical and Experimental Study. Inorg Chem. 2016 Oct 17;55(20):10284-10293. doi: 10.1021/acs.inorgchem.6b01550. Epub 2016 Sep 30. PMID: 27689907.
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Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization.

Chemistry (Weinheim an der Bergstrasse, Germany)

Li E, Hu Z, Song L, Yu W, Chang J.
PMID: 27355559
Chemistry. 2016 Jul 25;22(31):11022-7. doi: 10.1002/chem.201601744. Epub 2016 Jun 29.

A facile and efficient approach to access 1,2,4-triazolo[4,3-a]pyridines and related heterocycles has been accomplished through condensation of readily available aryl hydrazines with corresponding aldehydes followed by iodine-mediated oxidative cyclization. This transition-metal-free synthetic process is broadly applicable to a variety...

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Li E, Hu Z, Song L, et al. Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization. Chemistry. 2016;22(31):11022-7doi: 10.1002/chem.201601744.
Li, E., Hu, Z., Song, L., Yu, W., & Chang, J. (2016). Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization. Chemistry (Weinheim an der Bergstrasse, Germany), 22(31), 11022-7. https://doi.org/10.1002/chem.201601744
Li, Ertong, et al. "Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,31 (2016): 11022-7. doi: https://doi.org/10.1002/chem.201601744
Li E, Hu Z, Song L, Yu W, Chang J. Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization. Chemistry. 2016 Jul 25;22(31):11022-7. doi: 10.1002/chem.201601744. Epub 2016 Jun 29. PMID: 27355559.
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Facile Synthesis of Isoindolinones via Rh(III)-Catalyzed One-Pot Reaction of Benzamides, Ketones, and Hydrazines.

Organic letters

Zhang Y, Wang D, Cui S.
PMID: 25927906
Org Lett. 2015 May 15;17(10):2494-7. doi: 10.1021/acs.orglett.5b01016. Epub 2015 Apr 30.

A Rh(III)-catalyzed one-pot reaction of benzamides, ketones, and hydrazines for facile access to isoindolinones is reported. In this method, various ketones are transformed into donor-donor diazo compounds, which sequentially engage in insertion with benzamides under Rh(III) catalysis to generate...

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Zhang Y, Wang D, Cui S. Facile Synthesis of Isoindolinones via Rh(III)-Catalyzed One-Pot Reaction of Benzamides, Ketones, and Hydrazines. Org Lett. 2015;17(10):2494-7doi: 10.1021/acs.orglett.5b01016.
Zhang, Y., Wang, D., & Cui, S. (2015). Facile Synthesis of Isoindolinones via Rh(III)-Catalyzed One-Pot Reaction of Benzamides, Ketones, and Hydrazines. Organic letters, 17(10), 2494-7. https://doi.org/10.1021/acs.orglett.5b01016
Zhang, Yan, et al. "Facile Synthesis of Isoindolinones via Rh(III)-Catalyzed One-Pot Reaction of Benzamides, Ketones, and Hydrazines." Organic letters vol. 17,10 (2015): 2494-7. doi: https://doi.org/10.1021/acs.orglett.5b01016
Zhang Y, Wang D, Cui S. Facile Synthesis of Isoindolinones via Rh(III)-Catalyzed One-Pot Reaction of Benzamides, Ketones, and Hydrazines. Org Lett. 2015 May 15;17(10):2494-7. doi: 10.1021/acs.orglett.5b01016. Epub 2015 Apr 30. PMID: 25927906.
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Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols.

Dalton transactions (Cambridge, England : 2003)

Gaona MÁ, Montilla F, Álvarez E, Galindo A.
PMID: 25756702
Dalton Trans. 2015 Apr 14;44(14):6516-25. doi: 10.1039/c5dt00358j.

Ligand precursors HL(R,Ph) (R = Me, Ph) were synthesised by condensation of acetylacetone and the corresponding N,N-substituted hydrazines and were characterised spectroscopically and structurally. Both in the solid state and in solution they behave as (Z)-keto-enehydrazines and this was...

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Gaona MÁ, Montilla F, Álvarez E, et al. Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols. Dalton Trans. 2015;44(14):6516-25doi: 10.1039/c5dt00358j.
Gaona, M. �. �., Montilla, F., Álvarez, E., & Galindo, A. (2015). Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols. Dalton transactions (Cambridge, England : 2003), 44(14), 6516-25. https://doi.org/10.1039/c5dt00358j
Gaona, Miguel Ángel, et al. "Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols." Dalton transactions (Cambridge, England : 2003) vol. 44,14 (2015): 6516-25. doi: https://doi.org/10.1039/c5dt00358j
Gaona MÁ, Montilla F, Álvarez E, Galindo A. Synthesis, characterization and structure of nickel and copper compounds containing ligands derived from keto-enehydrazines and their catalytic application for aerobic oxidation of alcohols. Dalton Trans. 2015 Apr 14;44(14):6516-25. doi: 10.1039/c5dt00358j. PMID: 25756702.
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A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines.

Organic letters

Wang X, Xue L, Wang Z.
PMID: 25032787
Org Lett. 2014 Aug 01;16(15):4056-8. doi: 10.1021/ol5018849. Epub 2014 Jul 17.

A three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines catalyzed by copper(II) acetate is reported, leading to N-aminosulfonamides in good yields. Not only triethoxy(aryl)silanes but also triethoxy(alkyl)silanes are compatible during the process of insertion of sulfur dioxide. Additionally, diethoxydiarylsilanes...

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Wang X, Xue L, Wang Z. A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines. Org Lett. 2014;16(15):4056-8doi: 10.1021/ol5018849.
Wang, X., Xue, L., & Wang, Z. (2014). A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines. Organic letters, 16(15), 4056-8. https://doi.org/10.1021/ol5018849
Wang, Xianbo, et al. "A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines." Organic letters vol. 16,15 (2014): 4056-8. doi: https://doi.org/10.1021/ol5018849
Wang X, Xue L, Wang Z. A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines. Org Lett. 2014 Aug 01;16(15):4056-8. doi: 10.1021/ol5018849. Epub 2014 Jul 17. PMID: 25032787.
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Synthesis and characterization of secondary nitrosamines from secondary amines using sodium nitrite and p-toluenesulfonic acid.

Chemistry, an Asian journal

Miró Sabaté C, Delalu H.
PMID: 25582458
Chem Asian J. 2015 Mar;10(3):674-8. doi: 10.1002/asia.201403182. Epub 2015 Jan 12.

We synthesized nitrosamines (R2N-NO) with R = iPr (1), nPr (2), nBu (3), and hydroxyethyl (4) from the amine using sodium nitrite/p-toluenesulfonic acid in CH2Cl2. The rate of formation of 1-4 increases in the direction iPr

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Miró Sabaté C, Delalu H. Synthesis and characterization of secondary nitrosamines from secondary amines using sodium nitrite and p-toluenesulfonic acid. Chem Asian J. 2015;10(3):674-8doi: 10.1002/asia.201403182.
Miró Sabaté, C., & Delalu, H. (2015). Synthesis and characterization of secondary nitrosamines from secondary amines using sodium nitrite and p-toluenesulfonic acid. Chemistry, an Asian journal, 10(3), 674-8. https://doi.org/10.1002/asia.201403182
Miró Sabaté, Carles, and Delalu, Henri. "Synthesis and characterization of secondary nitrosamines from secondary amines using sodium nitrite and p-toluenesulfonic acid." Chemistry, an Asian journal vol. 10,3 (2015): 674-8. doi: https://doi.org/10.1002/asia.201403182
Miró Sabaté C, Delalu H. Synthesis and characterization of secondary nitrosamines from secondary amines using sodium nitrite and p-toluenesulfonic acid. Chem Asian J. 2015 Mar;10(3):674-8. doi: 10.1002/asia.201403182. Epub 2015 Jan 12. PMID: 25582458.
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ROMPGEL scavengers: a high-loading supported anhydride for sequestering amines and hydrazines.

Organic letters

Arnauld T, Barrett AG, Cramp SM, Roberts RS, Zecri FJ.
PMID: 10990422
Org Lett. 2000 Aug 24;2(17):2663-6. doi: 10.1021/ol006191s.

[reaction: see text]A versatile method for sequestering excess amines and hydrazines is reported using a high-loading ROMPGEL anhydride polymer.

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Arnauld T, Barrett AG, Cramp SM, et al. ROMPGEL scavengers: a high-loading supported anhydride for sequestering amines and hydrazines. Org Lett. 2000;2(17):2663-6doi: 10.1021/ol006191s.
Arnauld, T., Barrett, A. G., Cramp, S. M., Roberts, R. S., & Zecri, F. J. (2000). ROMPGEL scavengers: a high-loading supported anhydride for sequestering amines and hydrazines. Organic letters, 2(17), 2663-6. https://doi.org/10.1021/ol006191s
Arnauld, et al. "ROMPGEL scavengers: a high-loading supported anhydride for sequestering amines and hydrazines." Organic letters vol. 2,17 (2000): 2663-6. doi: https://doi.org/10.1021/ol006191s
Arnauld T, Barrett AG, Cramp SM, Roberts RS, Zecri FJ. ROMPGEL scavengers: a high-loading supported anhydride for sequestering amines and hydrazines. Org Lett. 2000 Aug 24;2(17):2663-6. doi: 10.1021/ol006191s. PMID: 10990422.
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Intermolecular electron transfer reactivity determined from cross-rate studies.

Accounts of chemical research

Nelsen SF, Pladziewicz JR.
PMID: 11955053
Acc Chem Res. 2002 Apr;35(4):247-54. doi: 10.1021/ar0101077.

Electron-transfer cross-reactions between neutral molecules and their radical cations spanning a wide range of structural type and intrinsic reactivity have been analyzed using classical Marcus theory. The principal factor found to govern intrinsic reactivity is the inner-shell bond reorganization...

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Nelsen SF, Pladziewicz JR. Intermolecular electron transfer reactivity determined from cross-rate studies. Acc Chem Res. 2002;35(4):247-54doi: 10.1021/ar0101077.
Nelsen, S. F., & Pladziewicz, J. R. (2002). Intermolecular electron transfer reactivity determined from cross-rate studies. Accounts of chemical research, 35(4), 247-54. https://doi.org/10.1021/ar0101077
Nelsen, Stephen F, and Pladziewicz, Jack R. "Intermolecular electron transfer reactivity determined from cross-rate studies." Accounts of chemical research vol. 35,4 (2002): 247-54. doi: https://doi.org/10.1021/ar0101077
Nelsen SF, Pladziewicz JR. Intermolecular electron transfer reactivity determined from cross-rate studies. Acc Chem Res. 2002 Apr;35(4):247-54. doi: 10.1021/ar0101077. PMID: 11955053.
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Showing 1 to 12 of 293 entries