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. © 2014 Elsevier Ltd
Attanasi, O.A., De Crescentini, L., Filippone, P., Giorgi, G., Nicolini, S., Perrulli, F.R., et al. (2014). From targeted aza-Michael addition to linked azaheterocyclic scaffolds. TETRAHEDRON, 70(40), 7336-7343 [10.1016/j.tet.2014.07.038].
From targeted aza-Michael addition to linked azaheterocyclic scaffolds
Giorgi G.;
2014-01-01
Abstract
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. © 2014 Elsevier Ltd
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https://hdl.handle.net/11365/48559
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