Solvent-free microwave-assisted multi-component reaction for preparation of 2-amino-1-aryl-2-(cyclohex-1-enyl)ethanones as precursors of pseudoephedrine analogues.
Microwave irradiation of chloroacetylarenes and enamines induced an aza-Darzens reaction followed by rearrangement of the aziridinium intermediate to give (2-amino-3-alkenoyl)arenes that were reduced selectively to syn-beta-aminoalcohols as pseudo-ephedrine analogues.
Ma
Li-Jian
LJ
Department of Medicinal and Bioengineering Science, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
Inokuchi
Tsutomu
T
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D004809:Ephedrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D007659:Ketones; D004809:Ephedrine