Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine

Mitsunori Oda; Yuko Yamaga; Yoshimitsu Kumai; Akira Ohta; Ryuta Miyatake

doi:doi:10.11648/j.mc.20150302.11

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Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine

Mitsunori Oda, Yuko Yamaga, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake

Published in Modern Chemistry (Volume 3, Issue 2)

Received: 25 February 2015 Accepted: 9 March 2015 Published: 15 March 2015

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Abstract

The title compound, 2,6-bis(1-azaazulen-2-yl)pyridine (5), was synthesized by condensation between tropone (6) and 2,6-bis(pyridinioacetyl)pyridinium salt (7) in the presence of ammonium acetate. By slow addition of an acetic acid solution of the pyridinium salt 7 to a mixture of 6 and ammonium acetate the yield of 5 was improved. Physical properties of 5 were investigated. It is worthy to note that upon irradiation 5 shows strong emission in acidic media in contrast to very weak emission in neutral media.

Published in	Modern Chemistry (Volume 3, Issue 2)
DOI	10.11648/j.mc.20150302.11
Page(s)	14-17
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2015. Published by Science Publishing Group

Keywords

Pincer-Type Ligand, Azaazulene, Pyridine, Tropone, Basicity, Emission Behavior

References

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[2]	G. van Koten, “Tuning the reactivity of metals held in a rigid ligand environment”, Pure & Appl. Chem. 1989, 61, 1681–1684.
[3]	J. T. Singleton, “The uses of pincer complexes in organic synthesis”, Tetrahedron 2003, 59, 1837–1857.
[4]	N. Selander and K. J. Szabó, “Catalysis by palladium pincer complexes”, Chem. Rev. 2011, 111, 2048–2076.
[5]	F, Kröhnke, “The specific synthesis of pyridines and oligopyridines”, Synthesis 1976, 89, 1–24.
[6]	N. Abe and T. Gunji, “The chemistry of azaazulenes”, Heterocycles 2010, 82, 201–248
[7]	N. Abe, “Recent progress in the chemistry of azaazulenes”, Recent Res. Devel. Org. & Bioorg. Chem. 2001, 4, 17–48.
[8]	M. Kimura, “The chemistry of aza-azulenes”, J. Synth. Org. Chem. Jpn. 1981, 39, 690–700
[9]	T. Nishiwaki and N. Abe, “Recent progress in the chemistry of azaazulenes: Synthetic methodology and chemical reactions”, Heterocycles 1981, 15, 547–582
[10]	M. Oda, K. Ogura, N. Chung T., S. Kishi, S. Kuroda, K. Fujimori, T. Noda, and N. Abe, “Synthesis and properties of 2-(2-pyridyl)-1-azaazulene”, Tetrahedron Lett. 2007, 48, 4471–4475.
[11]	M. Oda, D. Miyawaki, N. Matsumoto, and S. Kuroda, “Palladium-catalyzed amination of 2-chloro-1-azaazulene with 2-aminopyridine”, Heterocycles 2011, 83, 547–554.
[12]	M. Oda, A. Sugiyama, R. Takeuchi, Y. Fujiwara, R. Miyatake, T. Abe, and S. Kuroda, “Synthesis, molecular structure, and properties of 2-(2-hydroxyphenyl)-1-azaazulene”, Eur. J. Org. Chem. 2012, 2231–2236.
[13]	I. Sasaki, J. C. Daran, and G. G. A. Balavoine, “An effective route to polysubstituted symmetric terpyridines”, Synthesis 1999, 815–820.
[14]	Y. Sugimura, N. Soma, and Y. Kishida, “The reaction of troponoid with ylide. III. The reaction of tropone with pyridinium compounds”, Bull. Chem. Soc. Jpn. 1972, 45, 3174–3178.
[15]	The value of pKb3 could not be obtained because of its spectral change without isosbestic points in strong acidic media.
[16]	Emission quantum yields of 5 in CH3CN and EtOH are less than 1 x 10–3%. The yields were determined by comparison with that of anthracene (0.27 in EtOH).
[17]	K. R. Dahnke and L. A. Paquette, “Inverse electron-demand Diels-Alder cycloaddition of a ketene dithioacetal. Copper hydride-promoted reduction of a conjugated enone. 9-Dithiolanobicyclo[3.2.2]non-6-en-2-one from tropone”, Org. Synth. Coll. Vol. 9, 1998, 396–400.

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APA Style

Mitsunori Oda, Yuko Yamaga, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake. (2015). Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine. Modern Chemistry, 3(2), 14-17. https://doi.org/10.11648/j.mc.20150302.11

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ACS Style

Mitsunori Oda; Yuko Yamaga; Yoshimitsu Kumai; Akira Ohta; Ryuta Miyatake. Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine. Mod. Chem. 2015, 3(2), 14-17. doi: 10.11648/j.mc.20150302.11

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AMA Style

Mitsunori Oda, Yuko Yamaga, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake. Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine. Mod Chem. 2015;3(2):14-17. doi: 10.11648/j.mc.20150302.11

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@article{10.11648/j.mc.20150302.11,
  author = {Mitsunori Oda and Yuko Yamaga and Yoshimitsu Kumai and Akira Ohta and Ryuta Miyatake},
  title = {Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine},
  journal = {Modern Chemistry},
  volume = {3},
  number = {2},
  pages = {14-17},
  doi = {10.11648/j.mc.20150302.11},
  url = {https://doi.org/10.11648/j.mc.20150302.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20150302.11},
  abstract = {The title compound, 2,6-bis(1-azaazulen-2-yl)pyridine (5), was synthesized by condensation between tropone (6) and 2,6-bis(pyridinioacetyl)pyridinium salt (7) in the presence of ammonium acetate. By slow addition of an acetic acid solution of the pyridinium salt 7 to a mixture of 6 and ammonium acetate the yield of 5 was improved. Physical properties of 5 were investigated. It is worthy to note that upon irradiation 5 shows strong emission in acidic media in contrast to very weak emission in neutral media.},
 year = {2015}
}

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TY  - JOUR
T1  - Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine
AU  - Mitsunori Oda
AU  - Yuko Yamaga
AU  - Yoshimitsu Kumai
AU  - Akira Ohta
AU  - Ryuta Miyatake
Y1  - 2015/03/15
PY  - 2015
N1  - https://doi.org/10.11648/j.mc.20150302.11
DO  - 10.11648/j.mc.20150302.11
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 14
EP  - 17
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20150302.11
AB  - The title compound, 2,6-bis(1-azaazulen-2-yl)pyridine (5), was synthesized by condensation between tropone (6) and 2,6-bis(pyridinioacetyl)pyridinium salt (7) in the presence of ammonium acetate. By slow addition of an acetic acid solution of the pyridinium salt 7 to a mixture of 6 and ammonium acetate the yield of 5 was improved. Physical properties of 5 were investigated. It is worthy to note that upon irradiation 5 shows strong emission in acidic media in contrast to very weak emission in neutral media.
VL  - 3
IS  - 2
ER  -

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Author Information

Mitsunori Oda

Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, Nagano, Japan
Yuko Yamaga

Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, Nagano, Japan
Yoshimitsu Kumai

Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, Nagano, Japan
Akira Ohta

Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, Nagano, Japan
Ryuta Miyatake

Centre for Environmental Conservation and Research Safety, University of Toyama, Gofuku, Toyama, Japan

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APA Style

Mitsunori Oda, Yuko Yamaga, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake. (2015). Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine. Modern Chemistry, 3(2), 14-17. https://doi.org/10.11648/j.mc.20150302.11

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ACS Style

Mitsunori Oda; Yuko Yamaga; Yoshimitsu Kumai; Akira Ohta; Ryuta Miyatake. Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine. Mod. Chem. 2015, 3(2), 14-17. doi: 10.11648/j.mc.20150302.11

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AMA Style

Mitsunori Oda, Yuko Yamaga, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake. Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine. Mod Chem. 2015;3(2):14-17. doi: 10.11648/j.mc.20150302.11

Copy | Download

@article{10.11648/j.mc.20150302.11,
  author = {Mitsunori Oda and Yuko Yamaga and Yoshimitsu Kumai and Akira Ohta and Ryuta Miyatake},
  title = {Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine},
  journal = {Modern Chemistry},
  volume = {3},
  number = {2},
  pages = {14-17},
  doi = {10.11648/j.mc.20150302.11},
  url = {https://doi.org/10.11648/j.mc.20150302.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20150302.11},
  abstract = {The title compound, 2,6-bis(1-azaazulen-2-yl)pyridine (5), was synthesized by condensation between tropone (6) and 2,6-bis(pyridinioacetyl)pyridinium salt (7) in the presence of ammonium acetate. By slow addition of an acetic acid solution of the pyridinium salt 7 to a mixture of 6 and ammonium acetate the yield of 5 was improved. Physical properties of 5 were investigated. It is worthy to note that upon irradiation 5 shows strong emission in acidic media in contrast to very weak emission in neutral media.},
 year = {2015}
}

Copy | Download

TY  - JOUR
T1  - Synthesis and Properties of 2,6-Bis(1-Azaazulen-2-yl)-Pyridine
AU  - Mitsunori Oda
AU  - Yuko Yamaga
AU  - Yoshimitsu Kumai
AU  - Akira Ohta
AU  - Ryuta Miyatake
Y1  - 2015/03/15
PY  - 2015
N1  - https://doi.org/10.11648/j.mc.20150302.11
DO  - 10.11648/j.mc.20150302.11
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 14
EP  - 17
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20150302.11
AB  - The title compound, 2,6-bis(1-azaazulen-2-yl)pyridine (5), was synthesized by condensation between tropone (6) and 2,6-bis(pyridinioacetyl)pyridinium salt (7) in the presence of ammonium acetate. By slow addition of an acetic acid solution of the pyridinium salt 7 to a mixture of 6 and ammonium acetate the yield of 5 was improved. Physical properties of 5 were investigated. It is worthy to note that upon irradiation 5 shows strong emission in acidic media in contrast to very weak emission in neutral media.
VL  - 3
IS  - 2
ER  -

Copy | Download