A method for the synthesis of derivatives of [1, 3]thiazolo[3,2-a]pyridines, pyrido[2,1-b][1, 3]benzo-thiazole, [1, 3, 4]thiadiazolo[3,2-a]pyridine, and [1, 2, 4]triazolo[4,3-a]pyridine, which includes base initiated cyclization of quaternary azolium salts, formed by the interaction of (Z)-1,3-diaryl-4-bromo-2-buten-1-ones with 1-alkyl-1H-1,2,4-triazoles, 4-methyl-1,3-thiazole, 1,3-benzothiazole, and N-phenyl-1,3,4-thiadiazole-2-amine. Derivatives of 2-chloroimidazo[1,2-a]pyridine were obtained when 5-chloro-1-methyl-1H-imidazole was used.
Similar content being viewed by others
References
A. Johnson, J. Org. Chem., 41, 836 (1976)
S. V. Litvinenko, Yu. M. Volovenko, and F. S. Babichev, Khim. Geterotsikl. Soedin., 1528 (1992). [Chem. Heterocycl. Comp., 28, 1307 (1992)].
V. Kuzmenko and V. Komissarov, Khim. Geterotsikl. Soedin., 1497 (1981). [Chem. Heterocycl., Comp., 17, 1090 (1981)].
K. Sato, S. Arai, and T. Yamagishi, J. Heterocycl. Chem., 33, 57 (1996).
L. Potikha, V. Kovtunenko, A. Turelyk, A. Turov, and A. Tolmachev, Synth. Commun, 38, 2016 (2008).
L. M. Potikha, A. R. Turelyk, V. A. Kovtunenko, and A. V. Turov, Khim. Geterotsikl. Soedin., 95 (2010). [Chem. Heterocycl. Comp., 46, 82 (2010)].
H. H. Wassermann and N. E. Aubrey, J. Am. Chem. Soc., 75, 96 (1953).
L. M. Potikha, A. R. Turelyk, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 1478 (2009). [Chem. Heterocycl. Comp., 45, 1184 (2009)].
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, 275-287, February, 2010.
Rights and permissions
About this article
Cite this article
Potikha, L.M., Turelyk, A.R., Kovtunenko, V.A. et al. Synthesis of diarylazolo[a]pyridines from [(Z)-2,4-diaryl-4-oxo-2-butenyl]azolium salts. Chem Heterocycl Comp 46, 223–231 (2010). https://doi.org/10.1007/s10593-010-0495-0
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-010-0495-0