Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 2, Pages 1161-1167Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2021949
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Funding
- Ministero dell'Istruzione, dell'Universita e della Ricerca (MIUR)-Roma
- University of Urbino Carlo Bo
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By highly efficient, one-pot, three-component reactions, combining one set of 1,2-diaza-1,3-dienes (DDs), primary amines, and isothiocyanates in a different sequential order of addition, heterocyclic skeletal diversity can be achieved. The key feature discriminating the different heterocyclic core formation is the availability of the N or S heteronucleophile to give the first Michael addition step affording regioselective substituted 2-thiohydantoins or 2-iminothiazolidinones. The hydrazone or enehydrazino side chain at the 5-position of both heterocycles represents a valuable functionality to reach novel 5-hydroxyethylidene derivatives difficult to obtain by other methods.
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