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1,3-Thiazolidine derivatives from regioselective [2+3]-cycloadditions of azomethine ylides with thioketones


Domagala, Malgorzata; Linden, Anthony; Olszak, Tomasz A; Mlostoń, Grzegorz; Heimgartner, Heinz (2003). 1,3-Thiazolidine derivatives from regioselective [2+3]-cycloadditions of azomethine ylides with thioketones. Acta Crystallographica. Section C: Crystal Structure Communications, C59(5):o250-o253.

Abstract

The title compounds, namely dimethyl (2RS)-2,3-diphenyl-1,3-thiazolidine-5-spiro-20-adamantane-4,4-dicarboxylate methanol solvate, C28H31NO4S . 0.275CH4O, and dimethyl (4RS)-3,4-di-phenyl-1,3-thiazolidine-5-spiro-9' -(9'H-fluorene)-2,2-dicarboxylate, C31H25NO4S, were obtained from dipolar [2+3]-cycloadditions of an azomethine ylide with adamantanethione and thiofluorenone, respectively. The structures show that the choice of thioketone affects the regioselectivity of the cycloaddition. The asymmetric unit of the former structure contains two molecules of the thiazolidine derivative plus a site for a partial occupancy (55%) methanol molecule. O-H...O and C-H...O interactions link two of each of these entities into closed centrosymmetric hexamers. The five- membered ring in each structure has an envelope conformation.

Abstract

The title compounds, namely dimethyl (2RS)-2,3-diphenyl-1,3-thiazolidine-5-spiro-20-adamantane-4,4-dicarboxylate methanol solvate, C28H31NO4S . 0.275CH4O, and dimethyl (4RS)-3,4-di-phenyl-1,3-thiazolidine-5-spiro-9' -(9'H-fluorene)-2,2-dicarboxylate, C31H25NO4S, were obtained from dipolar [2+3]-cycloadditions of an azomethine ylide with adamantanethione and thiofluorenone, respectively. The structures show that the choice of thioketone affects the regioselectivity of the cycloaddition. The asymmetric unit of the former structure contains two molecules of the thiazolidine derivative plus a site for a partial occupancy (55%) methanol molecule. O-H...O and C-H...O interactions link two of each of these entities into closed centrosymmetric hexamers. The five- membered ring in each structure has an envelope conformation.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > General Biochemistry, Genetics and Molecular Biology
Language:English
Date:2003
Deposited On:19 Aug 2013 06:51
Last Modified:24 Jan 2022 01:22
Publisher:Wiley-Blackwell
ISSN:0108-2701
Funders:Polish State Committee for Scientific Research (KBN grant No. 3 TO) A007 16)
OA Status:Green
Publisher DOI:https://doi.org/10.1107/S0108270103006504
PubMed ID:12743406

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