Direct synthesis of polyfunctionalized unsaturated delta-lactones and delta-lactams from alpha-alkenoyl alpha-carboxyl/carbamoyl ketene S,S-acetals under Vilsmeier conditions.
An efficient method for direct synthesis of polyfunctionalized unsaturated delta-lactones 2 and delta-lactams 4 has been developed from the reaction of the easily available alpha-alkenoyl alpha-carboxyl/carbamoyl ketene S,S-acetals 1/3 and Vilsmeier reagents (DMF/POCl(3) or DMF/PBr(3)) via a cyclization followed by a halovinylation or haloformylation sequence.
Liu
Jun
J
Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
Wang
Mang
M
Han
Feng
F
Liu
Yingjie
Y
Liu
Qun
Q
D000080:Acetals / Q000737:chemistry*; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry*
D000080:Acetals; D005030:Ethylenes; D007659:Ketones; D007769:Lactams; D007783:Lactones; D013455:Sulfur; C008223:ketene