From targeted aza-Michael addition to linked azaheterocyclic scaffolds

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...

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Bibliographic Details
Published in:Tetrahedron 2014-10, Vol.70 (40), p.7336-7343
Main Authors: Attanasi, Orazio A., De Crescentini, Lucia, Filippone, Paolino, Giorgi, Gianluca, Nicolini, Simona, Perrulli, Francesca R., Santeusanio, Stefania
Format: Article
Language:English
Subjects:
Aza-Michael addition
Heteroannulation
Hydantoin
Multi-component reaction
Spiro compounds
Thiohydantoin
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.07.038