title: Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany.
authors.forename: Viktor A
authors.initials: VA
authors.lastname: Zapol'skii
authors.affiliation: Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany.
authors.forename: Jan C
authors.initials: JC
authors.lastname: Namyslo
authors.affiliation: Institute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Str. 4, 38678 Clausthal-Zellerfeld, Germany.
authors.forename: Mimoza
authors.initials: M
authors.lastname: Gjikaj
authors.affiliation: Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany.
authors.forename: Dieter E
authors.initials: DE
authors.lastname: Kaufmann
keywords: 1H-pyrazoles; 2-nitroperchlorobutadiene; atropisomers; cyclization; thiazolidin-4-ones