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Synthesis of a series of tetraminic acid sulfone analogs
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 con...
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Published in: | Monatshefte für Chemie 2017, Vol.148 (5), p.939-946 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | 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 |
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ISSN: | 0026-9247 1434-4475 |
DOI: | 10.1007/s00706-016-1884-6 |