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Title: | 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 |
Authors: | 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. |
Issue Date: | 2013 |
Citation: | 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 / E. V. Sadchikova, V. A. Bakulev, J. O. Subbotina [et al.] // Tetrahedron. — 2013. — Vol. 69. — № 34. — P. 6987-6992. |
Abstract: | 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. |
Keywords: | COVALENCE RATIO FACTOR CYCLOADDITION DIAZOAZOLES NONBONDED SA⋯O INTERACTION THIATRIAZINES IMIDAZOLE DERIVATIVE ISOTHIOCYANIC ACID DERIVATIVE OXYGEN PYRAZOLE DERIVATIVE PYRROLE DERIVATIVE SULFUR TRIAZINE DERIVATIVE ARTICLE CARBON NUCLEAR MAGNETIC RESONANCE CHEMICAL BOND CRYSTAL STRUCTURE CYCLOADDITION DENSITY FUNCTIONAL THEORY MOLECULAR INTERACTION MOLECULAR STABILITY PRIORITY JOURNAL PROTON NUCLEAR MAGNETIC RESONANCE QUANTUM CHEMISTRY SYNTHESIS X RAY DIFFRACTION |
URI: | http://elar.urfu.ru/handle/10995/27464 |
SCOPUS ID: | 84880137100 |
WOS ID: | 000322098000006 |
PURE ID: | 880400 |
ISSN: | 0040-4020 |
DOI: | 10.1016/j.tet.2013.06.062 |
Appears in Collections: | Научные публикации ученых УрФУ, проиндексированные в SCOPUS и WoS CC |
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