Concise preparation of novel tricyclic chemotypes: fused hydantoin–benzodiazepines
2010; Elsevier BV; Volume: 51; Issue: 36 Linguagem: Inglês
10.1016/j.tetlet.2010.06.131
ISSN1873-3581
AutoresSteven Gunawan, Gary S. Nichol, Shashi Chappeta, Justin Dietrich, Christopher Hulme,
Tópico(s)Synthesis and biological activity
ResumoThe following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance is high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO(2) mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on aldehydes of choice will be revealed and a facile oxidation of final products to imidazolidenetriones briefly discussed.
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