Skip to main content
SpringerLink
Log in

Strategies and methods for the synthesis of pyridinocrownophanes (microreview)

  • HETEROCYCLES IN FOCUS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This review aims to highlight the most significant recent developments in the synthesis of pyridinofused azacrown ethers, which contain a minor azaheterocyclic moiety contributing its nitrogen atom to the macrocycle. This subfield of azacrown ethers draws constant attention of scientists over the last decades owing to their great theoretical and practical potential.1 Pyridinocrownophanes, azacrown ethers containing a pyridine subunit, are widely used as ligands for effective metal ion sequestration,2 as well as enantiomeric recognition.3 They are also excellent phase-transfer catalysts,1 membrane ion transporting vehicles,4 scaffolds for the design of organic sensors, nanosized on-off switches, and other molecular devices.5 Certain pyridinoazacrown compounds have been found to possess antibacterial6 and anticancer properties.7

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Aza-crown Macrocycles; J. Wiley & Sons: New York, 1993. (b) Pedersen, C. J. Angew. Chem. 1988, 100, 1053.

  2. Bradshow, J. S.; Izatt, R. M. Acc. Chem. Res. 1997, 30, 338.

    Article  Google Scholar 

  3. (a) Lévai, S.; Németh, T.; Fődi, T.; Kupai, J.; Tóth, T.; Huszthy, P.; Balogh, G. T. J. Pharm. Biomed. Anal. 2015, 115, 192. (b) Şeker, S.; Barış, D.; Arslan, N.; Turgut, Y.; Pirinççioğlu, N.; Toğrul, M. Tetrahedron: Asymmetry 2014, 25, 411. (c) Farkas, V.; Tóth, T.; Orosz, G.; Huszthy, P.; Hollósi, M. Tetrahedron: Asymmetry 2006, 17, 1883.

  4. Gokel, G. W.; Murillo, O. Acc. Chem. Res. 1996, 29, 425.

    Article  CAS  Google Scholar 

  5. (a) Costero, A. M.; Bañuls, M. J.; Aurell, M. J.; Ochando, L. E.; Doménech, A. Tetrahedron 2005, 61, 10309. (b) Crown Compounds: Toward Future Applications; Cooper, S. R., Ed.; VCH: Wienheim, 1992. (c) Natali, M.; Giordani, S. Chem. Soc. Rev., 2012, 41, 4010.

  6. An, H.; Wang, T.; Mohan, V.; Griffey, R. H.; Cook, P. D. Tetrahedron 1998, 54, 3999.

    Article  CAS  Google Scholar 

  7. Artemenko, A. G.; Kovdienko, N. A.; Kuz'min, V. E.; Kamalov, G. L.; Lozitskaya, R. N.; Fedchuk, A. S.; Lozitsky, V. P.; Dyachenko, N. S.; Nosach, L. N. Eksp. Onkol. 2002, 24, 123. Chem. Abstr. 2003, 138, 297068.

  8. (a) Truong, H. H.; Le, T. A.; Soldatenkov, A. T.; Golovsov, N. I.; Soldatova, S. A. Chem. Heterocycl. Compd. 2012, 47, 1317. [Khim. Geterotsikl. Soedin. 2011, 1586.] (b) Le, T. A.; Truong, H. H.; Nguyen, P. T. T.; Pham, H. T.; Kotsuba, V. E.; Soldatenkov, A. T.; Khrustalev, V. N.; Wodajo, A. T. Macroheterocycles 2014, 7, 386. (c) Le, T. A.; Truong, H. H.; Nguyen, T. T. P.; Dao, T. N.; To, H. T.; Pham, T. H.; Soldatenkov, A. T. Mendeleev Commun. 2015, 25, 224.

  9. Kamadi, M.; Shockravi, A.; Mohtasham, R.; Moghanlo, S. P. ARKIVOC 2014, (iv), 242.

  10. (a) Funaki, T.; Inokuma, S.; Ide, H.; Yonekura, T.; Nakamura, Y.; Nishimura, J. Tetrahedron Lett. 2004, 45, 2393. (b) Inokuma, S.; Ide, H.; Yonekura, T; Funaki, T.; Kondo, S.; Shiobara, S.; Yoshihara, T.; Tobita, S.; Nishimura, J. J. Org. Chem. 2005, 70, 1698. (c) Inokuma, S.; Kuramami, M.; Otsuki, S.; Shirakawa, T.; Kondo, S.; Nakamura, Y.; Nishimura, J. Tetrahedron 2006, 62, 10005. (d) Inokuma, S.; Yatsuzuka, T.; Ohtsuki, S.; Hino, S.; Nishimura, J. Tetrahedron 2007, 63, 5088. (e) Inokuma, S.; Ito, M.; Nishimura, J. Top. Heterocycl. Chem. 2008, 17, 43.

  11. (a) Kupai, J.; Lévai, S.; Antal, K.; Balogh, G. T.; Tóth, T.; Huszthy, P. Tetrahedron: Asymmetry 2012, 23, 415. (b) Lévai, S.; Németh, T.; Fodi, T.; Kupai, J.; Tóth, T.; Huszthy, P.; Balogh, G. T. J. Pharm. Biomed. Anal. 2015, 115, 192. (c) Horváth, G.; Huszthy, P.; Szarvas, S.; Szókán, G.; Redd, J. T.; Bradshaw, J. S.; Izatt, R. M. Ind. Eng. Chem. Res. 2000, 39, 3576. (d) Gerencsér, J.; Báthori, N.; Czugler, M.; Huszthy, P.; Nógrádi, M. Tetrahedron: Asymmetry 2003, 14, 2803. (e) Wong, W.-L.; Huang, K.-H.; Teng, P.-F.; Lee, C.-S.; Kwong, H.-L. Chem. Commun., 2004, 384. (f) Kupai, J.; Huszthy, P.; Katz, M.; Tóth, T. ARKIVOC 2012, (v), 134. (g) Huszthy, P.; Samu, E.; Vermes, B.; Mezey-Vándor, G.; Nógrádi, M.; Bradshaw, J. S.; Izatt, R. M. Tetrahedron 1999, 55, 1491. (h) Prodi, L.; Bolletta, F.; Moltalti, M.; Zaccheroni, N.; Huszthy, P.; Samu, E.; Vermes, B. New J. Chem. 2000, 24, 781. (i) Lacatos, S.; Fetter, J.; Bertha, F.; Moltalti, M.; Zacceroni, N.; Huszthy, P.; Tóth, T.; Farcas, V.; Orosz, G.; Hollósi, M. Tetrahedron 2008, 64, 1012.

  12. Marchand, A. P.; Chong, H.-S.; Alihodžić, S.; Watson, W. H.; Bodige, S. G. Tetrahedron 1999, 55, 9687.

    Article  CAS  Google Scholar 

  13. (a) Lee, C.-S.; Teng, P.-F.; Wong, W.-L.; Kwong, H.-L.; Chan, A. S. C. Tetrahedron 2005, 61, 7924. (b) Cox, B. G.; Hurwood, T. V.; Prodi, L.; Montalti, M.; Bolletta, F.; Watt, C. I. F. J. Chem. Soc., Perkin Trans. 2 1999, 289.

  14. Ozer, H.; Kocakaya, S. O.; Akgun, A.; Hoşgören, H.; Togrul, M. Tetrahedron: Asymmetry 2009, 20, 1541.

    Article  CAS  Google Scholar 

  15. (a) Costero, A. M.; Monrabal, E.; Andreu, C.; Martínez-Máňez, R.; Soto, J.; Padrilla-Tosta, M. J.; Pardo, T.; Ochando, L. E.; Amigó, J. M. J. Chem. Soc., Dalton Trans. 2000, 361. (b) Costero, A. M.; Aurell, M. J.; Bañuls, M. J.; Ochando, L. E.; Tamarit, F. J.; Doménech, A. J. J. Inclusion Phenom. Macrocyclic Chem. 2003, 45, 241. (c) Costero, A. M.; Bañuls, M. J.; Aurell, M. J.; Ochando, L. E.; Doménech, A. J. Tetrahedron 2005, 61, 10309.

  16. Zhao, B.; Wang, F. Q.; Xia, M.; Tian, L. J. Chin. Chem. Lett. 2001, 12, 31.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. University of Science, Vietnam National University, Ha Noi, 144 Xuan Thuy, Cau Giay, Hanoi, 10000, Vietnam

    Anh Tuan Le

  2. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Anatoly T. Soldatenkov

Authors
  1. Anh Tuan Le
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anatoly T. Soldatenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anh Tuan Le.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(3), 152–154

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Le, A.T., Soldatenkov, A.T. Strategies and methods for the synthesis of pyridinocrownophanes (microreview). Chem Heterocycl Comp 52, 152–154 (2016). https://doi.org/10.1007/s10593-016-1850-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1850-6

Keywords

Search

Navigation