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 S?O interaction
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- 作者：Elena V. Sadchikova ; Vasiliy A. Bakulev ; Julia O. Subbotina ; Darya L. Privalova ; Wim Dehaen ; Kristof Van Hecke ; Koen Robeyns ; Luc Van Meervelt ; Vladimir S. Mokrushin
- 关键词：Cycloaddition ; Diazoazoles ; Thiatriazines ; Nonbonded S?O interaction ; Covalence ratio factor
- 刊名：Tetrahedron
- 出版年：2013
- 出版时间：26 August, 2013
- 年：2013
- 卷：69
- 期：34
- 页码：6987-6992
- 全文大小：644 K
文摘
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 S?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.