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4-Thiazolidinones in Heterocyclic Synthesis:Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones.
- Source :
-
Molecules . Jun2012, Vol. 17 Issue 6, p6362-6385. 24p. 13 Diagrams, 3 Charts. - Publication Year :
- 2012
-
Abstract
- The 4-thiazolidinones 3a-d were used as a key intermediates for the synthesis of 2-arylimino-5-arylidene-4-thiazolidinones derivatives 7a-p via nucleophilic addition reactions with the arylidene malononitrile. Moreover the 4-thiazolidinones 3a and 3c condensed with the DMF-DMA to form the corresponding enamines 8 and 9 depending on the reaction conditions. Otherwise the 4-thiazolidinone 3b reacts regioselectively with DMF-DMA to afford the enaminones 10 and 11, respectively. The latter reacts with many heterocyclic amines affording polyfunctionally substituted fused pyrimidine derivatives 13-18. The enamine 8b was also reacted with the 3-amino-1,2,4-triazole to afford the acyclic product 19, which could not be further cyclized to the corresponding tricyclic system 20. Moreover the 4-thiazolidinone 3c reacted with the benzenediazonium chloride to afford the arylhydrazones 12. The X-ray single crystal technique was employed in this study for structure elucidation and Z/E potential isomerism configuration determination. The X-ray crystallographic analyses of eight products could be obtained, thus establishing with certainty the structures proposed in this work. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ENAMINES
*AMINO acids
*PYRIMIDINES
*CHEMICAL synthesis
*CRYSTALLOGRAPHY
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 17
- Issue :
- 6
- Database :
- Academic Search Index
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- 77651504
- Full Text :
- https://doi.org/10.3390/molecules17066362