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Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
- Source :
- Molecules, Volume 24, Issue 17, Molecules, 24 (17), Article: 3069, Molecules, Vol 24, Iss 17, p 3069 (2019)
- Publication Year :
- 2019
- Publisher :
- Multidisciplinary Digital Publishing Institute, 2019.
-
Abstract
- The reactions of dialkyl acetylenedicarboxylates with various 2-oxo-acenaphthoquinylidene- and 4-acetyl[2.2]paracyclophanylidene-thiosemicarbazones were investigated. Using simple experimental procedures, 1,3-Thiazolidin-4-ones derived from acenaphthequinone or [2.2]paracyclophane were obtained as major products in good yields. In the case of allyl derivative of acenaphthoquinylidene-thiosemicarbazones, a complex structure of tetramethyl 5-(2-(((Z,E)-N-allyl-N&prime<br />(2-oxoacenaphthylen-1(2H)-ylidene)carbamohydrazonoyl)thio)-1,2,3-tris-(methoxycarbonyl)-cyclopropyl)-4-methoxy-7-oxabicyclo[2.2.1]hepta-2,5-diene-1,2,3,6-tetracarboxylate was formed. Single crystal X-ray analysis was used as an efficient tool to confirm the structure of the synthesized compounds as well as different spectroscopic data (1H-NMR, 13C-NMR, 2D-NMR, mass spectrometry and elemental analysis). The mechanism of the obtained products was discussed.
- Subjects :
- THIOSEMICARBAZONES
DIMETHYL ACETYLENEDICARBOXYLATE
DERIVATIVES
Chemistry & allied sciences
116 Chemical sciences
HYDRAZINECARBOTHIOAMIDE
4-acetyl[2.2]paracyclophane
1,3-DIPOLAR CYCLOADDITION
THIAZOLIDIN-4-ONES
3-COMPONENT
lcsh:QD241-441
EFFICIENT SYNTHESIS
thiosemicarbazone
1,3-thiazolidinones
lcsh:Organic chemistry
DMAD tetramer
ANTIOXIDANT
ddc:540
acenaphthequinone
dialkyl-acetylenedicarboxylates
HETEROCYCLES
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.dedup.wf.001..df32d04ad9c79e36a298646e76bae679
- Full Text :
- https://doi.org/10.3390/molecules24173069