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Beilstein J. Org. Chem. 2014, 10, 1638–1644, doi:10.3762/bjoc.10.170
Graphical Abstract
Scheme 1: SNVin reactions of pentachloro-2-nitro-1,3-butadiene (1).
Scheme 2: Formation of thiazolidin-4-ones 7–19.
Figure 1: Hindered rotation in the case of ortho- or meta-substituted aniline precursors.
Figure 2: X-ray analysis of thiazolidin-4-one 11.
Scheme 3: Assumed mechanism for the formation of thiazolidin-4-ones 7–18.
Scheme 4: Substitution reactions of the precursors 3 and 5 with additional amines.
Scheme 5: Synthesis of 5-arylmethylidenethiazolidin-4-ones 22–26 and 1H-pyrazoles 27, 28.
Scheme 6: Assumed mechanism for the formation of 1H-pyrazole 27.
Scheme 7: Formation of ethyl propanoate 29 and subsequent reactions.