Synthesis of a series of tetraminic acid sulfone analogs

• Published in: Monatshefte für Chemie Vol. 148; no. 5; pp. 939 - 946
• Main Authors: Popova, Maria V., Dobrydnev, Alexey V., Dyachenko, Maksim S., Duhayon, Carine, Listunov, Dymytrii, Volovenko, Yulian M.
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 2017; Springer Nature B.V; Springer Verlag
• Subjects: Alkylation; Analytical Chemistry; Chemical Sciences; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Coordination chemistry; Diketones; Dimethyl acetals; Dimethylformamide; Esters; Inorganic Chemistry; Organic Chemistry; Original Paper; Physical Chemistry; Potassium; Spiro compounds; Theoretical and Computational Chemistry; Aminonitriles; X-ray structure determination; Amino acids; Cyclization; Sulfonamides; Spiro compounds
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-016-1884-6

We have introduced a strategy for the construction of spirocycloalkane 1λ
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-1
H
-1λ
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-1
H
-1λ
6
-isothiazole-1,1-diones were converted into the target spiro 1λ
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 1λ
6
-isothiazolidine-1,1,4-triones with
N
,
N
-dimethylformamide dimethyl acetal leads to the formation of spiro 5-[(
Z
)-(dimethylamino)methylidene]-1λ
6
-isothiazolidine-1,1,4-triones.
Graphical abstract