Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

Beilstein Journal of Organic Chemistry

Mimoza Gjikaj¹  Dieter E. Kaufmann²  Viktor A. Zapol’skii²  Jan C. Namyslo² 

[1] Institute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Str. 4, 38678 Clausthal-Zellerfeld, Germany;Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany;

关键词: atropisomers;    cyclization;    2-nitroperchlorobutadiene;    1H-pyrazoles;    thiazolidin-4-ones;   

DOI  :  10.3762/bjoc.10.170

来源: DOAJ

【 摘 要 】

The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene (1) provides an appropriate precursor for the synthesis of special thiazolidin-4-ones. Applying different anilines as the second constituent for the requisite cyclization step, a series of (Z)-2-allylidenethiazolidin-4-ones was obtained in yields up to 81%. Some subsequent reactions have been examined too, such as the formation of perfunctionalized 1H-pyrazoles upon treatment with hydrazine. Thiazolidinones are as well known for their physiological activities as for their application in optoelectronics.

【 授权许可】

Unknown