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Thermal reactions of tributyltin hydride with alpha-azido esters: unexpected intervention of tin triazene adducts under both nonradical and radical conditions.

The Journal of organic chemistry

Benati L, Bencivenni G, Leardini R, Minozzi M, Nanni D, Scialpi R, Spagnolo P, Zanardi G.
PMID: 15822963
J Org Chem. 2005 Apr 15;70(8):3046-53. doi: 10.1021/jo0478095.

Thermal reaction of various alpha-azido esters with Bu(3)SnH in refluxing benzene results in smooth production of 3-(tributylstannyl)-1-triazene adducts affording cyclized 1,2,3-triazol-4-ones in preference to reduced amines and thence provides a new useful method for the preparation of these triazole...

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Benati L, Bencivenni G, Leardini R, et al. Thermal reactions of tributyltin hydride with alpha-azido esters: unexpected intervention of tin triazene adducts under both nonradical and radical conditions. J Org Chem. 2005;70(8):3046-53doi: 10.1021/jo0478095.
Benati, L., Bencivenni, G., Leardini, R., Minozzi, M., Nanni, D., Scialpi, R., Spagnolo, P., & Zanardi, G. (2005). Thermal reactions of tributyltin hydride with alpha-azido esters: unexpected intervention of tin triazene adducts under both nonradical and radical conditions. The Journal of organic chemistry, 70(8), 3046-53. https://doi.org/10.1021/jo0478095
Benati, Luisa, et al. "Thermal reactions of tributyltin hydride with alpha-azido esters: unexpected intervention of tin triazene adducts under both nonradical and radical conditions." The Journal of organic chemistry vol. 70,8 (2005): 3046-53. doi: https://doi.org/10.1021/jo0478095
Benati L, Bencivenni G, Leardini R, Minozzi M, Nanni D, Scialpi R, Spagnolo P, Zanardi G. Thermal reactions of tributyltin hydride with alpha-azido esters: unexpected intervention of tin triazene adducts under both nonradical and radical conditions. J Org Chem. 2005 Apr 15;70(8):3046-53. doi: 10.1021/jo0478095. PMID: 15822963.
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Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate.

Organic letters

Scadeng O, Ferguson MJ, West FG.
PMID: 21126097
Org Lett. 2011 Jan 07;13(1):114-7. doi: 10.1021/ol102651k. Epub 2010 Dec 03.

Tetrasubstituted 1,4-dien-3-ones undergo Nazarov cyclization at low temperature, followed by reaction with organic azides via an apparent [3 + 3]-cycloaddition to give bridged bicyclic triazenes. These products do not appear to be intermediates in the previously described Schmidt-type process...

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Scadeng O, Ferguson MJ, West FG. Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate. Org Lett. 2010;13(1):114-7doi: 10.1021/ol102651k.
Scadeng, O., Ferguson, M. J., & West, F. G. (2011). Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate. Organic letters, 13(1), 114-7. https://doi.org/10.1021/ol102651k
Scadeng, Owen, et al. "Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate." Organic letters vol. 13,1 (2011): 114-7. doi: https://doi.org/10.1021/ol102651k
Scadeng O, Ferguson MJ, West FG. Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate. Org Lett. 2011 Jan 07;13(1):114-7. doi: 10.1021/ol102651k. Epub 2010 Dec 03. PMID: 21126097.
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Synthesis of triazenes with nitrous oxide.

Angewandte Chemie (International ed. in English)

Kiefer G, Riedel T, Dyson PJ, Scopelliti R, Severin K.
PMID: 25336431
Angew Chem Int Ed Engl. 2015 Jan 02;54(1):302-5. doi: 10.1002/anie.201408597. Epub 2014 Oct 21.

Triazenes are valuable compounds in organic chemistry and numerous applications have been reported. Furthermore, triazenes have been investigated extensively as potential antitumor drugs. Here, we describe a new method for the synthesis of triazenes. The procedure involves a reagent...

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Kiefer G, Riedel T, Dyson PJ, et al. Synthesis of triazenes with nitrous oxide. Angew Chem Int Ed Engl. 2014;54(1):302-5doi: 10.1002/anie.201408597.
Kiefer, G., Riedel, T., Dyson, P. J., Scopelliti, R., & Severin, K. (2015). Synthesis of triazenes with nitrous oxide. Angewandte Chemie (International ed. in English), 54(1), 302-5. https://doi.org/10.1002/anie.201408597
Kiefer, Gregor, et al. "Synthesis of triazenes with nitrous oxide." Angewandte Chemie (International ed. in English) vol. 54,1 (2015): 302-5. doi: https://doi.org/10.1002/anie.201408597
Kiefer G, Riedel T, Dyson PJ, Scopelliti R, Severin K. Synthesis of triazenes with nitrous oxide. Angew Chem Int Ed Engl. 2015 Jan 02;54(1):302-5. doi: 10.1002/anie.201408597. Epub 2014 Oct 21. PMID: 25336431.
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Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN.

Chemistry, an Asian journal

Klapötke TM, Kofen M, Schmidt L, Stierstorfer J, Wurzenberger MHH.
PMID: 34411440
Chem Asian J. 2021 Oct 04;16(19):3001-3012. doi: 10.1002/asia.202100714. Epub 2021 Sep 02.

For the first time, an adequate selective synthesis, circumventing the formation of 2-hydroxy-5H-tetrazole, of 1-hydroxy-5H-tetrazole (HTO), as well as the synthesis of bis(1-hydroxytetrazol-5-yl)triazene (H

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Klapötke TM, Kofen M, Schmidt L, et al. Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN. Chem Asian J. 2021;16(19):3001-3012doi: 10.1002/asia.202100714.
Klapötke, T. M., Kofen, M., Schmidt, L., Stierstorfer, J., & Wurzenberger, M. H. H. (2021). Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN. Chemistry, an Asian journal, 16(19), 3001-3012. https://doi.org/10.1002/asia.202100714
Klapötke, Thomas M, et al. "Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN." Chemistry, an Asian journal vol. 16,19 (2021): 3001-3012. doi: https://doi.org/10.1002/asia.202100714
Klapötke TM, Kofen M, Schmidt L, Stierstorfer J, Wurzenberger MHH. Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN. Chem Asian J. 2021 Oct 04;16(19):3001-3012. doi: 10.1002/asia.202100714. Epub 2021 Sep 02. PMID: 34411440; PMCID: PMC8518496.
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Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions.

Bioconjugate chemistry

Davis GJ, Townsend JA, Morrow MG, Hamie M, Shepard AJ, Hsieh CC, Marty MT, Jewett JC.
PMID: 34730351
Bioconjug Chem. 2021 Nov 17;32(11):2432-2438. doi: 10.1021/acs.bioconjchem.1c00459. Epub 2021 Nov 03.

This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized...

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Davis GJ, Townsend JA, Morrow MG, et al. Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions. Bioconjug Chem. 2021;32(11):2432-2438doi: 10.1021/acs.bioconjchem.1c00459.
Davis, G. J., Townsend, J. A., Morrow, M. G., Hamie, M., Shepard, A. J., Hsieh, C. C., Marty, M. T., & Jewett, J. C. (2021). Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions. Bioconjugate chemistry, 32(11), 2432-2438. https://doi.org/10.1021/acs.bioconjchem.1c00459
Davis, Garrett J, et al. "Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions." Bioconjugate chemistry vol. 32,11 (2021): 2432-2438. doi: https://doi.org/10.1021/acs.bioconjchem.1c00459
Davis GJ, Townsend JA, Morrow MG, Hamie M, Shepard AJ, Hsieh CC, Marty MT, Jewett JC. Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions. Bioconjug Chem. 2021 Nov 17;32(11):2432-2438. doi: 10.1021/acs.bioconjchem.1c00459. Epub 2021 Nov 03. PMID: 34730351.
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Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications.

Angewandte Chemie (International ed. in English)

Suleymanov AA, Severin K.
PMID: 33142011
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):6879-6889. doi: 10.1002/anie.202011031. Epub 2020 Nov 03.

Aromatic compounds containing triazenyl groups (N

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Suleymanov AA, Severin K. Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications. Angew Chem Int Ed Engl. 2020;60(13):6879-6889doi: 10.1002/anie.202011031.
Suleymanov, A. A., & Severin, K. (2021). Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications. Angewandte Chemie (International ed. in English), 60(13), 6879-6889. https://doi.org/10.1002/anie.202011031
Suleymanov, Abdusalom A, and Severin, Kay. "Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications." Angewandte Chemie (International ed. in English) vol. 60,13 (2021): 6879-6889. doi: https://doi.org/10.1002/anie.202011031
Suleymanov AA, Severin K. Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications. Angew Chem Int Ed Engl. 2021 Mar 22;60(13):6879-6889. doi: 10.1002/anie.202011031. Epub 2020 Nov 03. PMID: 33142011.
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Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles.

The Journal of organic chemistry

Kimball DB, Weakley TJ, Haley MM.
PMID: 12201760
J Org Chem. 2002 Sep 06;67(18):6395-405. doi: 10.1021/jo020229s.

A new route to isoindazoles and cinnolines through the cyclization of (2-alkynylphenyl)triazenes under neutral conditions is presented. The products that result from heating the starting triazenes depend on both the type of alkyne ortho to the triazene functionality and...

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Kimball DB, Weakley TJ, Haley MM. Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles. J Org Chem. 2002;67(18):6395-405doi: 10.1021/jo020229s.
Kimball, D. B., Weakley, T. J., & Haley, M. M. (2002). Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles. The Journal of organic chemistry, 67(18), 6395-405. https://doi.org/10.1021/jo020229s
Kimball, David B, et al. "Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles." The Journal of organic chemistry vol. 67,18 (2002): 6395-405. doi: https://doi.org/10.1021/jo020229s
Kimball DB, Weakley TJ, Haley MM. Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles. J Org Chem. 2002 Sep 06;67(18):6395-405. doi: 10.1021/jo020229s. PMID: 12201760.
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Synthesis and Characterization of Novel Bis-Triazenes: 3,8-Di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-Di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The Reaction of Diazonium Ions with Ethylenediamine/Formaldehyde Mixtures.

The Journal of organic chemistry

Peori MB, Vaughan K, Hooper DL.
PMID: 11672395
J Org Chem. 1998 Oct 16;63(21):7437-7444. doi: 10.1021/jo981276g.

Reaction of a diazonium salt solution with a mixture of ethylenediamine and an excess of formaldehyde or 1,3,6,8-tetraazatricyclo[4.4.1.1(3,8)]dodecane results in the formation of a novel class of bis-triazenes, the 3,8-di(2-aryl-1-azenyl)-1,3,6,8-tetraazabicyclo[4.4.1]undecanes (6), which have been fully characterized by spectroscopy, elemental...

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Peori MB, Vaughan K, Hooper DL. Synthesis and Characterization of Novel Bis-Triazenes: 3,8-Di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-Di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The Reaction of Diazonium Ions with Ethylenediamine/Formaldehyde Mixtures. J Org Chem. 1998;63(21):7437-7444doi: 10.1021/jo981276g.
Peori, M. B., Vaughan, K., & Hooper, D. L. (1998). Synthesis and Characterization of Novel Bis-Triazenes: 3,8-Di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-Di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The Reaction of Diazonium Ions with Ethylenediamine/Formaldehyde Mixtures. The Journal of organic chemistry, 63(21), 7437-7444. https://doi.org/10.1021/jo981276g
Peori, M. Brad, et al. "Synthesis and Characterization of Novel Bis-Triazenes: 3,8-Di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-Di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The Reaction of Diazonium Ions with Ethylenediamine/Formaldehyde Mixtures." The Journal of organic chemistry vol. 63,21 (1998): 7437-7444. doi: https://doi.org/10.1021/jo981276g
Peori MB, Vaughan K, Hooper DL. Synthesis and Characterization of Novel Bis-Triazenes: 3,8-Di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-Di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The Reaction of Diazonium Ions with Ethylenediamine/Formaldehyde Mixtures. J Org Chem. 1998 Oct 16;63(21):7437-7444. doi: 10.1021/jo981276g. PMID: 11672395.
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Efficient cleavage-cross-coupling strategy for solid-phase synthesis-a modular building system for combinatorial chemistry.

Angewandte Chemie (International ed. in English)

Bräse S, Schroen M.
PMID: 25138497
Angew Chem Int Ed Engl. 1999;38(8):1071-3. doi: 10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO;2-9.

A new modular building system for the combinatorial chemistry was developed on the basis of triazene linkers. Starting from an aniline system, further functional units and virtually any alkene or alkyne as terminator furnished lipophilic multicomponent systems in high...

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Bräse S, Schroen M. Efficient cleavage-cross-coupling strategy for solid-phase synthesis-a modular building system for combinatorial chemistry. Angew Chem Int Ed Engl. 1999;38(8):1071-3doi: 10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO;2-9.
Bräse, S., & Schroen, M. (1999). Efficient cleavage-cross-coupling strategy for solid-phase synthesis-a modular building system for combinatorial chemistry. Angewandte Chemie (International ed. in English), 38(8), 1071-3. https://doi.org/10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO;2-9
Bräse, S, and Schroen, M. "Efficient cleavage-cross-coupling strategy for solid-phase synthesis-a modular building system for combinatorial chemistry." Angewandte Chemie (International ed. in English) vol. 38,8 (1999): 1071-3. doi: https://doi.org/10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO;2-9
Bräse S, Schroen M. Efficient cleavage-cross-coupling strategy for solid-phase synthesis-a modular building system for combinatorial chemistry. Angew Chem Int Ed Engl. 1999;38(8):1071-3. doi: 10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO;2-9. PMID: 25138497.
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Synthesis and study of redox-active acyclic triazenes: toward electrochromic applications.

The Journal of organic chemistry

Ono RJ, Suzuki Y, Khramov DM, Ueda M, Sessler JL, Bielawski CW.
PMID: 21417488
J Org Chem. 2011 May 06;76(9):3239-45. doi: 10.1021/jo200139f. Epub 2011 Mar 22.

Coupling of various 4-substituted phenyl azides with two distinct quinone-containing N-heterocyclic carbenes (NHCs) afforded the respective mono- and ditopic 1,3-disubstituted acyclic triazenes in moderate to excellent yields (38-92%). Depending on their pendant substituents (derived from the azides), the acyclic...

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Ono RJ, Suzuki Y, Khramov DM, et al. Synthesis and study of redox-active acyclic triazenes: toward electrochromic applications. J Org Chem. 2011;76(9):3239-45doi: 10.1021/jo200139f.
Ono, R. J., Suzuki, Y., Khramov, D. M., Ueda, M., Sessler, J. L., & Bielawski, C. W. (2011). Synthesis and study of redox-active acyclic triazenes: toward electrochromic applications. The Journal of organic chemistry, 76(9), 3239-45. https://doi.org/10.1021/jo200139f
Ono, Robert J, et al. "Synthesis and study of redox-active acyclic triazenes: toward electrochromic applications." The Journal of organic chemistry vol. 76,9 (2011): 3239-45. doi: https://doi.org/10.1021/jo200139f
Ono RJ, Suzuki Y, Khramov DM, Ueda M, Sessler JL, Bielawski CW. Synthesis and study of redox-active acyclic triazenes: toward electrochromic applications. J Org Chem. 2011 May 06;76(9):3239-45. doi: 10.1021/jo200139f. Epub 2011 Mar 22. PMID: 21417488.
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The synthesis of 3-substituted 6-aryl-3 H-benzo[a][1,2,3]triazinones using polymer-bound triazenes.

Journal of combinatorial chemistry

Gil C, Schwögler A, Bräse S.
PMID: 14714982
J Comb Chem. 2004 Jan-Feb;6(1):38-42. doi: 10.1021/cc0340271.

No abstract available.

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Gil C, Schwögler A, Bräse S. The synthesis of 3-substituted 6-aryl-3 H-benzo[a][1,2,3]triazinones using polymer-bound triazenes. J Comb Chem. 2004;6(1):38-42doi: 10.1021/cc0340271.
Gil, C., Schwögler, A., & Bräse, S. (2004). The synthesis of 3-substituted 6-aryl-3 H-benzo[a][1,2,3]triazinones using polymer-bound triazenes. Journal of combinatorial chemistry, 6(1), 38-42. https://doi.org/10.1021/cc0340271
Gil, Carmen, et al. "The synthesis of 3-substituted 6-aryl-3 H-benzo[a][1,2,3]triazinones using polymer-bound triazenes." Journal of combinatorial chemistry vol. 6,1 (2004): 38-42. doi: https://doi.org/10.1021/cc0340271
Gil C, Schwögler A, Bräse S. The synthesis of 3-substituted 6-aryl-3 H-benzo[a][1,2,3]triazinones using polymer-bound triazenes. J Comb Chem. 2004 Jan-Feb;6(1):38-42. doi: 10.1021/cc0340271. PMID: 14714982.
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Friedel-Crafts arylation for the formation of C(sp2)-C(sp2) bonds: a route to unsymmetrical and functionalized polycyclic aromatic hydrocarbons from aryl triazenes.

Angewandte Chemie (International ed. in English)

Zhou J, Yang W, Wang B, Ren H.
PMID: 23124928
Angew Chem Int Ed Engl. 2012 Dec 03;51(49):12293-7. doi: 10.1002/anie.201206578. Epub 2012 Nov 04.

No abstract available.

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Zhou J, Yang W, Wang B, et al. Friedel-Crafts arylation for the formation of C(sp2)-C(sp2) bonds: a route to unsymmetrical and functionalized polycyclic aromatic hydrocarbons from aryl triazenes. Angew Chem Int Ed Engl. 2012;51(49):12293-7doi: 10.1002/anie.201206578.
Zhou, J., Yang, W., Wang, B., & Ren, H. (2012). Friedel-Crafts arylation for the formation of C(sp2)-C(sp2) bonds: a route to unsymmetrical and functionalized polycyclic aromatic hydrocarbons from aryl triazenes. Angewandte Chemie (International ed. in English), 51(49), 12293-7. https://doi.org/10.1002/anie.201206578
Zhou, Jun, et al. "Friedel-Crafts arylation for the formation of C(sp2)-C(sp2) bonds: a route to unsymmetrical and functionalized polycyclic aromatic hydrocarbons from aryl triazenes." Angewandte Chemie (International ed. in English) vol. 51,49 (2012): 12293-7. doi: https://doi.org/10.1002/anie.201206578
Zhou J, Yang W, Wang B, Ren H. Friedel-Crafts arylation for the formation of C(sp2)-C(sp2) bonds: a route to unsymmetrical and functionalized polycyclic aromatic hydrocarbons from aryl triazenes. Angew Chem Int Ed Engl. 2012 Dec 03;51(49):12293-7. doi: 10.1002/anie.201206578. Epub 2012 Nov 04. PMID: 23124928.
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