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Article Dans Une Revue Acta Crystallographica Section C : Structural Chemistry [2014-...] Année : 2018

New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies

Résumé

The synthesis of three new polysubstituted monoterpenic thiazolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(dimethylamino)methylidene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thiosemicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thiazolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical molecules within the asymmetric unit with the same absolute configuration. These two molecules are linked through N-H...O hydrogen bonds, building an R22(8) graph-set motif.
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Dates et versions

hal-02336707 , version 1 (29-10-2019)

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Abdellah N'Ait Ousidi, Moulay Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Anthony Robert, et al.. New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies. Acta Crystallographica Section C : Structural Chemistry [2014-..], 2018, 74 (12), pp.1629-1634. ⟨10.1107/S2053229618015802⟩. ⟨hal-02336707⟩
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