Gebert, Andreas; Linden, Anthony; Mlostoń, 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.
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.
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.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > General Chemistry |
| Language: | English |
| Date: | 2003 |
| Deposited On: | 09 Oct 2013 14:24 |
| Last Modified: | 30 Jul 2020 10:00 |
| Publisher: | Polskie Towarzystwo Chemiczne |
| ISSN: | 0137-5083 |
| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel |
| OA Status: | Closed |
| Project Information: |
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Gebert, Andreas