Synthesis 2015; 47(17): 2523-2528
DOI: 10.1055/s-0034-1380434
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the First Representatives of Spiro-1λ6-isothiazolidine-1,1,4-triones

Alexey V. Dobrydnev*
a  Chemistry Department, Taras Shevchenko National University of Kiev, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: alexey.pierrot@gmail.com
b  SMC Ecopharm Ltd., Naberezhno-Korchuvatska Street 136-B, Kyiv 03045, Ukraine
,
Maria V. Popova
a  Chemistry Department, Taras Shevchenko National University of Kiev, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: alexey.pierrot@gmail.com
,
Nathalie Saffon-Merceron
c  Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse Cedex 9, France
,
Dymytrii Listunov
a  Chemistry Department, Taras Shevchenko National University of Kiev, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: alexey.pierrot@gmail.com
d  CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse Cedex 4, France
,
Yulian M. Volovenko
a  Chemistry Department, Taras Shevchenko National University of Kiev, Lva Tolstoho Street 12, Kyiv 01033, Ukraine   Email: alexey.pierrot@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 30 March 2015

Accepted after revision: 28 May 2015

Publication Date:
25 June 2015 (eFirst)

Abstract

A strategy for the construction of spiro[cycloalkane-1,3′-1′λ6-isothiazolidine]-1′,1′,4′-triones through the sulfonylation of 1-aminocyclopropane- and 1-aminocyclobutanecarboxylates with methanesulfonyl chloride followed by alkylation with methyl iodide and subsequent cyclization in the presence of potassium tert-butoxide in N,N-dimethylformamide is reported. An efficient synthesis of starting 1-aminocyclopropane- and 1-aminocyclobutanecarboxylic acids was developed. The reaction of spiro[cycloalkane-1,3′-1′λ6-isothiazolidine]-1′,1′,4′-triones with N,N-dimethylformamide dimethyl acetal (DMF­DMA) gives 5′-[(Z)-(dimethylamino)methylene]spiro[cycloalkane-1,3′-1′λ6-isothiazolidine]-1′,1′,4′-triones, the structure of which was confirmed by X-ray diffraction study.

Primary Data

 
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