Synthesis of a series of tetraminic acid sulfone analogs

Maria V. Popova (1, 2) , Alexey V. Dobrydnev (1) , Maksim S. Dyachenko (1, 2) , Carine Guyard-Duhayon (3) , Dymytrii Listunov (3, 4) , Yulian M. Volovenko (5)

1 Department of Chemistry, Taras Shevchenko National University of Kyiv
2 Enamine Ltd
3 LCC - Laboratoire de chimie de coordination
4 UT3 - Université Toulouse III - Paul Sabatier
5 National Taras Shevchenko University of Kiev

We have introduced a strategy for the construction of spirocycloalkane 1 lambda(6)-isothiazolidine-1,1,4-triones through the mesylation of 1-aminocyclopentane-, 1-aminocyclohexane-, and 1-aminocycloheptanecarboxylic acid esters with methanesulfonylchloride followed by alkylation with methyl iodide and consequent cyclization in the presence of potassium tert-butoxide in N,N-dimethylformamide. The spirocycloalkane 4-amino-2,3-dihydro-1H-1 lambda(6)-isothiazole-1,1-diones were prepared via mesylation of N-methylated 1-aminocyclopentyl-, 1-aminocyclohexyl-, and 1-aminocycloheptyl carbonitriles followed by treatment of obtained N-(1-cyanocycloalkyl)-N-methylmethanesulfonamides with potassium tert-butoxide in N,N-dimethylformamide. The spiro 4-amino-2,3-dihydro-1H-1 lambda(6)-isothiazole-1,1-diones were converted into the target spiro 1 lambda(6)-isothiazolidine-1,1,4-triones by acid-catalyzed hydrolysis. The structure of a target spiro compound and its isolated key intermediate was confirmed by X-ray diffraction study. The interaction of spiro 1 lambda(6)-isothiazolidine-1,1,4-triones with N,N-dimethylformamide dimethyl acetal leads to the formation of spiro 5-[(Z)-(dimethylamino)methylidene]-1 lambda(6)-isothiazolidine-1,1,4-triones.

Domaines: Chimie de coordination

Maria V. Popova, Alexey V. Dobrydnev, Maksim S. Dyachenko, Carine Guyard-Duhayon, Dymytrii Listunov, et al.. Synthesis of a series of tetraminic acid sulfone analogs. Chemical Monthly = Monatshefte für Chemie, 2017, 148 (5), pp.939-946. ⟨10.1007/s00706-016-1884-6⟩. ⟨hal-01948253⟩