An efficient method for the synthesis of nitropiperidones.
A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha,beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.
Ruano
José Luis García
JL
Departamento de Química OrgAnica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
Haro
Teresa de
Td
Singh
Rajinder
R
Cid
M Belén
MB
D003500:Cyclization; D017611:Fluorine Compounds / Q000138:chemical synthesis / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D017611:Fluorine Compounds; D009574:Nitro Compounds; D010881:Piperidones