N-methylated 5-alkenyloxazolium salt transformations.
[reaction: see text] In the course of natural product synthetic studies, 5-(4-pentenyl)oxazole and 5-(5-hexenyl)oxazole were N-methylated. The initial N-methylated 5-alkenyloxazolium salt adducts were found to be only intermediates and were ultimately transformed into hydroindole and hydroisoquinoline compounds, respectively.
Wenkert
D
D
Department of Chemistry, University of North Texas, Denton, Texas 76203-5068, USA. wenkert@msu.edu
Chen
T F
TF
Ramachandran
K
K
Valasinas
L
L
Weng Ll
McPhail
A T
AT
D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008745:Methylation; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*
D007211:Indoles; D007546:Isoquinolines; D010080:Oxazoles