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Reaction of thioureidomethylenebisphosphonic acids with α-haloketones: I. Effect of substituents on the reaction pathway

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Abstract

Substituted thioureidomethylenebisphosphonic acids react with haloketones to form thiazoles. The cyclization direction is predictably controlled by the size of the substituent. The NMR spectra of the resulting isomeric tetrazoles have well-defined differences and allow reliable structural assessment of the products.

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References

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Correspondence to A. L. Chuiko.

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Original Russian Text © A.L. Chuiko, L.P. Filonenko, M.O. Lozinskii, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 1, pp. 59–68.

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Chuiko, A.L., Filonenko, L.P. & Lozinskii, M.O. Reaction of thioureidomethylenebisphosphonic acids with α-haloketones: I. Effect of substituents on the reaction pathway. Russ J Gen Chem 79, 57–66 (2009). https://doi.org/10.1134/S1070363209010095

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  • DOI: https://doi.org/10.1134/S1070363209010095

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