Research Article

Classical Benzotriazole-Mediated α-Aminoalkylations of Alkynes: Synthesis and Characterization of Alk-2-yn-1-amines as Amphiphilic Materials

Krzysztof R. Idzik

Wroclaw University of Technology, Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Joanna Cabaj,

Joanna Cabaj

Wroclaw University of Technology, Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Jadwiga Sołoducho,

Jadwiga Sołoducho

[email protected]

Wroclaw University of Technology, Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Ashraf A. A. Abdel-Fattah,

Ashraf A. A. Abdel-Fattah

Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt

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Krzysztof R. Idzik,

Krzysztof R. Idzik

Wroclaw University of Technology, Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Joanna Cabaj,

Joanna Cabaj

Wroclaw University of Technology, Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Jadwiga Sołoducho,

Jadwiga Sołoducho

[email protected]

Wroclaw University of Technology, Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Ashraf A. A. Abdel-Fattah,

Ashraf A. A. Abdel-Fattah

Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt

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First published: 25 September 2007

https://doi.org/10.1002/hlca.200790173

Citations: 4

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Abstract

Reactions of readily available and stable benzotriazolemethanamines 1a–l, obtained from aldehydes and secondary amines (Scheme 2), gave the expected alk-2-yn-1-amines 3a–t (Scheme 3). The amphiphilic character of the synthesized products was responsible for physicochemical measurements. Specific aggregation properties of the obtained compounds make them useful as electroactive materials in the Langmuir–Blodgett technique.

References

1 M. Tramontini, L. Angiolini, ‘Mannich Bases – Chemistry and Uses’, CRC, 1994, p. 304.
Google Scholar
2 M. Tramontini, L. Angiolino, Tetrahedron 1990, 46, 1791.
10.1016/S0040-4020(01)89752-0
CAS Web of Science® Google Scholar
3 P. Traxler, U. Trinks, E. Buchdunger, H. Mett, T. Meyer, M. Muller, J. Rosel, N. Lydon, J. Med. Chem. 1995, 38, 2441.
10.1021/jm00013a020
CAS PubMed Web of Science® Google Scholar
4 T. Lóránd, E. Ösz, G. Kispál, G. Nagy, E. Weckert, D. Luebbert, A. Meents, B. Kocsis, L. Prökai, Arkivoc 2004, vii, 34.
Google Scholar
5 J. Sapi, J. Y. Laronze, Arkivoc 2004, vii, 208.
10.3998/ark.5550190.0005.717
Google Scholar
6 M. Tramontini, Synthesis 1973, 12, 703.
10.1055/s-1973-22294
Google Scholar
7 M. Arend, B. Westermann, N. Risch, Angew. Chem., Int. Ed. 1998, 37, 1044.
10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E
CAS PubMed Web of Science® Google Scholar
8 S. Piper, N. Risch, Arkivoc 2003, i, 86.
10.3998/ark.5550190.0004.111
Google Scholar
9 A. R. Katritzky, X. Lan, J. Z. Yang, O. V. Denisko, Chem. Rev. 1998, 98, 409.
10.1021/cr941170v
CAS PubMed Web of Science® Google Scholar
10 A. R. Katritzky, K. Manju, S. Singh, N. K. Meher, Tetrahedron 2005, 61, 2555.
10.1016/j.tet.2004.12.018
CAS Web of Science® Google Scholar
11 A. R. Katritzky, K. Yannakopoulou, W. Kuzmierkiewicz, J. M. Aurrecoechea, G. J. Palenik, A. E. Koziol, M. Szczesniak, R. Skarjune, J. Chem. Soc., Perkin Trans. 1 1987, 2673.
10.1039/p19870002673
CAS Web of Science® Google Scholar
12 A. R. Katritzky, K. Yannakopoulou, P. Lue, D. Rasala, L. Urogdi, J. Chem. Soc., Perkin Trans. 1 1989, 225.
10.1039/p19890000225
CAS Web of Science® Google Scholar
13 A. R. Katritzky, S. K. Nair, G. Qiu, Synthesis 2002, 2, 199.
10.1055/s-2002-19801
Google Scholar
14 A. R. Katritzky, S. Strah, S. A. Belyakov, Tetrahedron 1998, 54, 7167.
10.1016/S0040-4020(98)00353-6
CAS Web of Science® Google Scholar
15 G. G. Roberts, ‘Langmuir-Blodgett Films’, Plenum Press, New York, 1990.
Google Scholar
16 C. F. Shu, R. Dodda, F. L. Wu, M. S. Liu, A. K. Y. Jen, Macromolecules 2003, 36, 6698.
10.1021/ma030123e
CAS Web of Science® Google Scholar
17 A. R. Katritzky, K. Manju, S. K. Singh, N. K. Meher, Tetrahedron 2005, 61, 2555.
10.1016/j.tet.2004.12.018
CAS Web of Science® Google Scholar
18 A. R. Katritzky, K. R. Idzik, A. A. A. Abdel-Fattaha, J. Sołoducho, P. J. Steel, Synthesis 2006, 20, 3377.
10.1055/s-2006-949463
CAS Web of Science® Google Scholar
19 J. Cabaj, K. Idzik, J. Sołoducho, A. Chyla, Tetrahedron 2006, 62, 758.
10.1016/j.tet.2005.09.142
CAS Web of Science® Google Scholar
20 J. P. Gotteland, I. Brunel, F. Gendre, J. Desire, A. Delhon, D. Junquero, P. Oms, S. Halazy, J. Med. Chem. 1995, 38, 3207.
10.1021/jm00017a004
CAS PubMed Web of Science® Google Scholar
21 J. Cabaj, J. Sołoducho, A. Nowakowska, A. Chyla, Electroanalysis 2006, 18, 801.
10.1002/elan.200503463
CAS Web of Science® Google Scholar
22 J. Doskocz, M. Doskocz, S. Roszak, J. Sołoducho, J. Leszczynski, J. Phys. Chem. A 2006, 110, 13989.
10.1021/jp0658896
CAS PubMed Web of Science® Google Scholar

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Volume90, Issue9

September 2007

Pages 1672-1680

Classical Benzotriazole-Mediated α-Aminoalkylations of Alkynes: Synthesis and Characterization of Alk-2-yn-1-amines as Amphiphilic Materials

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Classical Benzotriazole-Mediated α-Aminoalkylations of Alkynes: Synthesis and Characterization of Alk-2-yn-1-amines as Amphiphilic Materials

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