Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles
| Autor: | Grzegorz Mlostoń, Paulina Grzelak, Maciej Mikina, Anthony Linden, Heinz Heimgartner |
|---|---|
| Přispěvatelé: | Mlostoń Grzegorz, Department of Organic and Applied Chemistry, University of Łódź, Grzelak Paulina, Department of Organic and Applied Chemistry, University of Łódź, Mikina Maciej, Center of Molecular and Macromolecular Studies PAS, Linden Anthony, Department of Chemistry, University of Zürich, Winterthurerstrasse, Heimgartner Heinz, Department of Chemistry, University of Zürich, Winterthurerstrasse, University of Zurich, Mlostoń, Grzegorz |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
10120 Department of Chemistry
high pressure reactions Full Research Paper lcsh:QD241-441 chemistry.chemical_compound Shift sequence hetero-Diels–Alder reactions lcsh:Organic chemistry 540 Chemistry Diels alder Organic chemistry methyl propiolate thiopyrans lcsh:Science Thiopyran Chemistry Methyl propiolate Aryl Organic Chemistry Regioselectivity thioketones dimethyl acetylenedicarboxylate (DMAD) lcsh:Q 1605 Organic Chemistry |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 11, Iss 1, Pp 576-582 (2015) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones. The authors thank the National Science Center (Cracow, Poland) for generous financial support (Grant Maestro-3 (Dec- 2012/06/A/ST5/00219). Skilful performance of microanalyses by Ms Hanna Jatczak and Ms Agnieszka Cieślińska (University of Łódź) is gratefully acknowledged |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|