A novel three-component butenolide synthesis.
[reaction: see text]. 5-Acylamino butenolides can be assembled by a multicomponent reaction (MCR) of isocyanides, glyoxals, and acetophosphonic acid diethylesters, followed by a intramolecular Wittig-type reaction. The reaction can be performed either in one pot or with the isolation of the intermediate Passerini product. This versatile reaction offers three independent inputs displayed in the final product. Applications in combinatorial chemistry and natural product synthesis can be envisioned.
Beck
B
B
Morphochem AG, Gmunderstr. 37-37a, 81379 München, Germany.
Magnin-Lachaux
M
M
Herdtweck
E
E
Dömling
A
A
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D003486:Cyanides / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006037:Glyoxal / Q000737:chemistry; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry
D003486:Cyanides; D005663:Furans; D007166:Immunosuppressive Agents; D006037:Glyoxal; C004511:butenolide; D015107:4-Butyrolactone