Synthesis of alpha-amino-alpha'-diazomethyl ketones via ring opening of substituted cyclopropanones with alkyl azides. A facile route to N-substituted 3-azetidinones.
[reaction: see text] The reaction of alkyl azides with triethyl(1-methoxy-2, 2-dimethyl-cyclopropoxy)silane affords a series of alpha-amino-alpha'-diazomethyl ketones in moderate yields (38-54%). The mechanism of this novel process is discussed. The diazomethyl ketones could also be cyclized to the corresponding N-substituted 3-azetidinones in good yield upon treatment with Rh(2)(OAc)(4).
Desai
P
P
Departments of Medicinal Chemistry and Chemistry, The University of Kansas, Lawrence 66045-2506, USA.
Aubé
J
J
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D000924:Anticholesteremic Agents / Q000138:chemical synthesis; D001384:Azetidines / Q000138:chemical synthesis; D001386:Azides / Q000138:chemical synthesis; D003521:Cyclopropanes / Q000737:chemistry; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C116379:2-azetidinone; D000588:Amines; D000924:Anticholesteremic Agents; D001384:Azetidines; D001386:Azides; D003521:Cyclopropanes; C015795:diazomethyl ketones; D003978:Diazomethane