Journal
TETRAHEDRON
Volume 70, Issue 40, Pages 7336-7343Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.07.038
Keywords
Aza-Michael addition; Multi-component reaction; Hydantoin; Thiohydantoin; Heteroannulation; Spiro compounds
Categories
Funding
- Ministero dell'Istruzione, dell'Universita e della Ricerca (MIUR)-Roma
- University of Urbino Carlo Bo
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A straightforward method for the synthesis of spaced, phenyl-linked bis(thiohydantoin) derivatives and (thio)hydantoins spiro-fused to pyrroline ring has been developed. All the synthetic strategies here presented rely on initial aza-Michael addition followed by acylation/regioselective ring-closure step involving DD, primary amine and iso(thio)cyanate in a 3-CR providing 1,3,5-trisubstituted (thio)hydantoins. The choice of opportune acyclic reagents in the sequential 3-CR followed by 1,4-nucleophilic addition/intramolecular ring closing and 1,3-dipolar cycloaddition permits a number of C-N and C-C formation that realizes different kind of linkage between several pharmacophores. (C) 2014 Elsevier Ltd. All rights reserved.
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