Abstract
The 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 are 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 CO2-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed.
Original language | English (US) |
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Pages (from-to) | 4689-4692 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 51 |
Issue number | 36 |
DOIs | |
State | Published - Sep 8 2010 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry