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On cyclization of 2-chloro-N-phenacylpyridinium ylides by the action of aryldiazonium salts

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2-chloro-N-phenacylpyridinium salts with diazonium salts in the presence of bases was studied for the first time. It was demonstrated that this reaction leads to the formation of [1,2,4]triazolo[4,3-a]pyridinium salts. It was shown that substitution of the pyridine with a thiazole moiety leads to a similar cyclization.

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References

  1. 1 (a) Yoshimura, Y.; Tomimatsu, K.; Nishimura, T.; Miyake, A.; Hashimoto, N. J. Antibiotics 1992, 45, 721. (b) Sadana, A. K.; Mirza, Y.; Aneja, K. R.; Prakash, O. Eur. J. Med. Chem. 2003, 38, 533. (c) Ivashchenko, A. A.; Savchuk, N. F.; Tkachenko, S. E. RU Pattent 2534804. (d) Lawson, E. C.; Hoekstra, W. J.; Addo, M. F.; Andrade-Gordon, P.; Damiano, B. P.; Kauffman, J. A.; Mitchell, J. A.; Maryanoff, B. E. Bioorg. Med. Chem. Lett. 2001, 11, 2619.

  2. 2 (a) Schmidt, M. A.; Qian, X. Tetrahedron Lett. 2013, 54, 5721. (b) Reichelt, A.; Falsey, J. R.; Rzasa, R. M.; Thiel, O. R.; Achmatowicz, M. M.; Larsen, R. D.; Zhang, D. Org. Lett., 2010, 12, 792. (c) Nakka, M.; Tadikonda, R.; Rayavarapu, S.; Sarakula, P.; Vidavalur, S. Synthesis 2015, 517. (d) Shawali, A. S. ARKIVOC 2010, (i), 33.

  3. 3 (a) Potikha, L. M.; Turelyk, A. R.; Kovtunenko, V. A.; Turov, A. V.; Palamarchuk, G. V.; Zubatyuk, R. I.; Shishkin, O. V. Chem. Heterocycl. Compd. 2010, 46, 742. [Khim. Geterotsikl. Soedin. 2010, 919.] (b) Potikha, L. M.; Turelyk, A. R.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2011, 47, 1436. [Khim. Geterotsikl. Soedin. 2011, 1725.] (c) Potikha, L. M.; Turelyk, A. R.; Shelepyuk, A. V.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2012, 48, 343. [Khim. Geterotsikl. Soedin. 2012, 364.]

  4. 4 Paudler W. W.; Brumbaugh, R. J. J. Heterocycl. Chem. 1968, 5, 29.

  5. 5 (a) Fathi, T.; Dinh An, N.; Schmitt, G.; Vebrel, J.; Laude, B. Bull. Soc. Chim. Belg. 1987, 96(2), 145. (b) Gunic, E.; Tabakovic, I. J. Org. Chem. 1988, 53, 5081. (c) Schantl, J. G.; Hebeisen, P. Tetrahedron 1990, 46(2), 395. (d) Grubert, L.; Jugelt, W.; Bres, H. J.; Köppel, H.; Strietzel, U.; Dombrowski, A. Liebigs Ann. Chem. 1992, 885.

  6. 6 Babaev, E. V. Chem. Heterocycl. Compd. 2016, 52, 666. [Khim. Geterotsikl. Soedin. 2016, 666.]

  7. 7 Babaev, E. V. Dr. Chem. Thesis; Moscow, 2007.

  8. 8 Kröhnke, F. Ber. 1935, 68, 1177.

  9. 9 Venkataraman, K. The Chemistry of Synthetic Dyes [Russian translation]; GNTI Khim. Lit.: Leningrad, 1956, Vol. 1, p. 250.

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Correspondence to Eugene V. Babaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 727–729

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Topchiy, M.A., Babaev, E.V. On cyclization of 2-chloro-N-phenacylpyridinium ylides by the action of aryldiazonium salts. Chem Heterocycl Comp 52, 727–729 (2016). https://doi.org/10.1007/s10593-016-1955-y

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  • DOI: https://doi.org/10.1007/s10593-016-1955-y

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