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Synthesis, structure and properties of novel N-thiophosphorylated derivatives of 1,3-dihydro-2H-benzimidazol-2-imine and imidazolidine-2-imine |
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| Authors: | Felix D. Sokolov Damir A. Safin Nail G. Zabirov Alexander Yu. Verat Vasiliy V. Brusko Dmitry B. Krivolapov Ekaterina V. Mironova Igor A. Litvinov |
| Affiliation: | aDepartment of Chemistry, Kazan State University, Kremlevskaya Street 18, 420008 Kazan, Tatarstan, Russia bArbusov Institute of Organic and Physical Chemistry, Arbuzov Street 8, 420088 Kazan, Tatarstan, Russia |
| Abstract: | The reaction of bis-thiourea o-C6H4[NHC(S)NHP(S)(Oi-Pr)2]2 (1) with iodine, KOH and ClCH2C(O)OCH3 leads to O,O′-diisopropyl-1,3-dihydro-2H-benzimidazol-2-ylideneamidothiophosphate (2) formation. The complex of the potassium salt of compound 2 with 18-crown-6, having the composition [K(18-crown-6)L], has been synthesized. Bis-thiourea [CH2NHC(S)NHP(S)(Oi-Pr)2]2 (6) forms a stable potassium salt, which oxidation by iodine leads to a product of heterocyclization, O,O′-diisopropyl-(1-{[(diisopropoxyphosphorothio)amino]carbonothioyl}imidazolidine-2-ylidene)amidothiophosphate (8), in which one of the thiourea fragments is kept. |
| Keywords: | Heterocycles Crown-ether Crystal structures Phosphorylated derivatives Thioureas |
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