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Synthesis of N-Unsubstituted 1,3-Thiazolidines by [2+3]-Cycloaddition of an Azomethine Ylide with Thiocarbonyl Compounds


Gebert, Andreas; Linden, Anthony; Mloston, Grzegorz; Heimgartner, Heinz (2003). Synthesis of N-Unsubstituted 1,3-Thiazolidines by [2+3]-Cycloaddition of an Azomethine Ylide with Thiocarbonyl Compounds. Polish Journal of Chemistry, 77:157-167.

Abstract

1,3-Dipolar cycloadditions of azomethine ylides with thiocarbonyl compounds have been used for the preparation of N-unsubstituted 1,3-thiazolidines. The reactive 1-phenyl-N-(trimethylsilyl)azomethine ylide (1c) was generated in situ by treatment of N-(benzylidene)[(trimethylsilyl)methyl]amine (6) with trimethylsilyl triflate and CsF in HMPA. All cycloadditions proceeded non-regioselectively, which led to mixtures of 4-phenyl- and 2-phenyl-substituted 1,3-thiazolidines.

Abstract

1,3-Dipolar cycloadditions of azomethine ylides with thiocarbonyl compounds have been used for the preparation of N-unsubstituted 1,3-thiazolidines. The reactive 1-phenyl-N-(trimethylsilyl)azomethine ylide (1c) was generated in situ by treatment of N-(benzylidene)[(trimethylsilyl)methyl]amine (6) with trimethylsilyl triflate and CsF in HMPA. All cycloadditions proceeded non-regioselectively, which led to mixtures of 4-phenyl- and 2-phenyl-substituted 1,3-thiazolidines.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2003
Deposited On:09 Oct 2013 14:24
Last Modified:05 Apr 2016 17:02
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel

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