Hetero-Diels-Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

被引：7

作者：

Mloston, Grzegorz ^{[1
]}

Grzelak, Paulina ^{[1
]}

Mikina, Maciej ^{[2
]}

Linden, Anthony ^{[3
]}

Heimgartner, Heinz ^{[3
]}

机构：

[1] Univ Lodz, Dept Organ & Appl Chem, PL-91403 Lodz, Poland

[2] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland

[3] Univ Zurich, Dept Chem, CH-8057 Zurich, Switzerland

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷

关键词：

dimethyl acetylenedicarboxylate (DMAD); hetero-Diels-Alder reactions; high pressure reactions; methyl propiolate; thioketones; thiopyrans; 1,3-DIPOLAR CYCLOADDITIONS; HETEROAROMATIC THIOKETONES; ANTIPROLIFERATIVE ACTIVITY; SULFUR-HETEROCYCLES; MULTIPLE BONDS; THIOBENZOPHENONE; THIOPYRAN; THIONES; BREAST;

D O I：

10.3762/bjoc.11.63

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：576 / 582

页数：7

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