СИНТЕЗ И НЕКОТОРЫЕ ХИМИЧЕСКИЕ СВОЙСТВА 2,2-ДИМЕТИЛ-4-R-1-ОКСА-4-АЗА-2-СИЛАБЕНЗОЦИКЛОГЕПТАН-5-ОНОВ

Abstract

One-pot synthesis of 2,2-dimethyl-4-R-1-oxa-4-aza-2-sila-5-benzocycloheptanones (R = Me, CH₂SiMe₂Cl) from the N-methylamide of salicylic acid and salicylamide, respectively, by treatment of these amides with a mixture of hexamethyldisilazane and dimethylchloromethylchlorosilane was developed. The hydrolysis and other nucleophilic substitution reactions of the resultant seven-membered silacyclanes were studied. In the case of the silacyclane with R = Me, hydrolysis leads to the corresponding disiloxane, while the silacyclane with R = CH₂SiMe₂Cl gives either 2,2,6,6-tetramethyl-4-(2-hydroxybenzoyl)-2,6-disilamorpholine or its hydrochloride, depending on the reaction conditions. The chlorine atom was replaced by fluorine in the silacyclane with R = CH₂SiMe₂Cl. The structures of 2,2,6,6-tetramethyl-4-(2-hydroxybenzoyl)-2,6-disilamorpholine and its hydrochloride as well as 2,2-dimethyl-4-R-1-oxa-4-aza-2-sila-5-benzocycloheptanones (R = CH₂SiMe₂Cl, CH₂SiMe₂F) were confirmed by X-ray diffraction.

How to Cite
Zamyshlyaeva, O. A.; Shipov, A. G.; Kramarova, E. P.; Negrebetsky, Vad. V.; Shumskii, A. N.; Tandura, S. N.; Bylikin, S. Yu.; Ovchinnikov, Yu. E.; Pogozhikh, S. A.; Baukov, Yu. I. Chem. Heterocycl. Compd. 2002, 38, 116. [Khim. Geterotsikl. Soedin. 2002, 127.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1014871813405