From targeted aza-Michael addition to linked azaheterocyclic scaffolds

Autor:	Paolino Filippone, Gianluca Giorgi, Simona Nicolini, Francesca R. Perrulli, Stefania Santeusanio, Orazio A. Attanasi, Lucia De Crescentini
Rok vydání:	2014
Předmět:	Organic Chemistry Regioselectivity Hydantoin Thio Pyrroline Ring (chemistry) Biochemistry Combinatorial chemistry Cycloaddition chemistry.chemical_compound chemistry Drug Discovery Michael reaction Multi-component reaction
Zdroj:	Tetrahedron. 70:7336-7343
ISSN:	0040-4020
DOI:	10.1016/j.tet.2014.07.038
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4593c63d8bb16980c642092942989357 https://doi.org/10.1016/j.tet.2014.07.038 Zobrazit plný text záznamu Full Text from ScienceDirect