| Autor: |
Gagarin AA; Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russian Federation., Suntsova PO; Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russian Federation., Minin AS; Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russian Federation.; M. N. Mikheev Institute of Metal Physics, Ural Branch of Russian Academy of Science, 18 South Kovalevskaya Street, Yekaterinburg 620219, Russian Federation., Pozdina VA; Institute of Immunology and Physiology, Pervomayskaya Str. 106, Ekaterinburg 620049, Russian Federation., Slepukhin PA; Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Science, 22 South Kovalevskaya Street, Yekaterinburg 620219, Russian Federation., Benassi E; Shihezi University, 280 North Fourth Road, Shihezi, Xinjiang 832000, China., Belskaya NP; Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russian Federation.; Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Science, 22 South Kovalevskaya Street, Yekaterinburg 620219, Russian Federation. |
| Abstrakt: |
Reactions of penta-2,4-dienethioamides with acetylenedicarboxylic acid, methyl and ethyl esters, and methyl propiolate were systematically studied, and a number of new 2,3-dihydro-5 H -thiazolo[3,2- a ]pyridines (DTPs) and 4 H ,6 H -pyrido[2,1- b ][1,3]thiazines (PTZs) were prepared. A possible mechanism for a multistep domino transformation is suggested, and the key step is the 1,6-electrocyclic reaction. An additional alternative method for the synthesis of new heterocyclic systems was achieved. Evidence of the electrocyclic mechanism of a key step was collected from the analysis of the spatial structure of the synthesized bicyclic nonaromatic pyridines by X-ray diffraction and quantum chemical calculations, as well as from the thermodynamic quantities. DTPs exhibited yellow fluorescence in solution and yellow to red emissions in the solid state. Biological investigations demonstrated the ability of DTPs to penetrate living and fixed cells and presumably accumulate in lysosomes. |
