Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5] thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by Sa⋯O interaction
(2013) Tetrahedron — Vol. 69, n° 34, p. 6987-6992 (2013)
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- 5-Diazoimidazoles and 5-diazopyrazoles have been shown to react with acyl isothiocyanates yielding the imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines stabilized by a nonbonded Sa⋯O interaction. In contrast to acyl isothiocyanates, alkyl-, aryl-, and arylsulfonyl isothiocyanates do not react with 5-diazoazoles. The nature and the strength of stabilizing intramolecular interaction between non-bonded S and O atoms have been studied by X-ray analysis for mono crystals and DFT calculations for selected azolo[5,1-d][1,2,3,5] thiatriazines. The interaction was described in terms of Weinhold covalence ratio factors, NBO, and AIM schemes. The reaction discovered was used to develop an efficient approach toward the new 8-substituted 4-ethoxycarbonylimino-4- benzoyl- and 4-(3,4,5,6-tetrafluorobenzoyl)iminoimidazo(pyrazolo)[5,1-d][1,2,3, 5]thiatriazines. © 2013 Elsevier Ltd. All rights reserved.
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Sadchikova, E. V., Bakulev, V. A., Subbotina, J. O., Privalova, D. L., Dehaen, W., Van Hecke, K., Robeyns, K., Van Meervelt, L., & Mokrushin, V. S. (2013). Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5] thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by Sa⋯O interaction. Tetrahedron, 69(34), 6987-6992. https://doi.org/10.1016/j.tet.2013.06.062 (Original work published 2013)