Object's details: Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

Provider:Repozytorium Uniwersytetu Łódzkiego

Description

Title:
Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles
Creator:
Mloston, Grzegorz;
Grzelak, Paulina;
Mikina, Maciej;
Linden, Anthony;
Heimgartner, Heinz
Contributor:
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;
gmloston@uni.lodz.pl;
heinz.heimgartner@chem.uzh.ch
Description:
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
Object availability:
free access
Rights:
Uznanie autorstwa 3.0 Polska;
http://creativecommons.org/licenses/by/3.0/pl
Date:
2015.09.28;
2015.04.28
Type:
Article
Language:
English
Format:
application/pdf
Publisher:
Beilstein Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Relation:
Beilstein Journal of Organic Chemistry;2015;
11
Subject:
dimethyl acetylenedicarboxylate (DMAD);
hetero-Diels–Alder reactions;
high pressure reactions; methyl propiolate;
thioketones;
thiopyrans
Identifier:
1860-5397;
http://hdl.handle.net/11089/11998 ;
10.3762/bjoc.11.63
Data provider:
Repozytorium Uniwersytetu Łódzkiego

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Object's details: Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

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