It has been shown that the reaction of epichlorhydrin with 3-hydroxybenzimidazo[2,1-b]thiazanium salts leads to recyclization of the thiazanium ring with the formation of substituted 1-(2,3-epithiopropyl)benzimidazol-2-ones in high yield. The proposed method enables the introduction of functional groups unstable in alkaline medium into the structure of thiirane derivatives.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. P. Bandgar, N. S. Joshi, and V. T. Kamble, Tetrahedron Lett., 47, 4775 (2006).
B. Das, V. Saidi Reddy, and M. Krishnaiah, Tetrahedron Lett., 47, 8471 (2006).
A. Bellomo and D. Gonzalez, Tetrahedron Lett.,48, 3047 (2007).
E. Lukowska and J. Plenkiewicz, Tetrahedron: Asymmetry, 18, 493 (2007).
E. Lukowska and J. Plenkiewicz, Tetrahedron: Asymmetry, 18, 1202 (2007).
E. Rogers, H. Araki, L. A. Batory, C. E. McInnis, and J. T. Njardarson, J. Am. Chem. Soc., 129, 2768 (2007).
S. Komiya, S. Muroi, M. Furuya, and M. Hirano, J. Am. Chem. Soc., 122, 170 (2000).
N. I. Korotkikh, Zh. Org. Khim., 25, 1533 (1989).
N. I. Korotkikh, A. F. Aslanov, and O. P. Shvaika, Zh. Org. Khim., 26, 1761 (1990).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 440-444, March, 2010.
Rights and permissions
About this article
Cite this article
Orlov, M.A., Aslanov, A.F. & Korotkikh, N.I. Recyclization of benzimidazo[2,1-b]thiazanium salts into 1-(2,3-epithiopropyl)benzimidazol-2-ones under the action of epichlorhydrin. Chem Heterocycl Comp 46, 347–350 (2010). https://doi.org/10.1007/s10593-010-0511-4
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-010-0511-4