Aromatic allylation via diazotization: variation of the allylic moiety and a short route to a benzazepine derivative.
A continued study of the recently discovered diazotizative allylation (DiazAll) reaction of aniline derivatives is reported. Several allyl reagents, commonly used in radical allylation reactions, were evaluated, and some of these reagents resulted in allylation when used in the DiazAll reaction. The best result was obtained with allyl bromide. Substituted allylic bromides gave the corresponding allyl aromatic compounds in poor to excellent yields. In comparison with an established method for aromatic allylation, the DiazAll reaction performed well and was superior when a more complex allylic bromide was used. Finally, a new allylation-bromocyclization reaction was demonstrated and used in the synthesis of a known inhibitor of phenylethanolamine N-methyltransferase (PNMT), an enzyme involved in the biosynthesis of adrenaline.
Ek
Fredrik
F
Organic Chemistry 1, Department of Chemistry, Lund University, P.O. Box 124, S-221 00 Lund, Sweden.
Wistrand
Lars-Göran
LG
Frejd
Torbjörn
T
D000498:Allyl Compounds / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001552:Benzazepines / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D004837:Epinephrine / Q000378:metabolism; D006842:Hydrocarbons, Brominated / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010625:Phenylethanolamine N-Methyltransferase / Q000037:antagonists & inhibitors
D000498:Allyl Compounds; D000814:Aniline Compounds; D001552:Benzazepines; D006842:Hydrocarbons, Brominated; D007202:Indicators and Reagents; D010625:Phenylethanolamine N-Methyltransferase; D004837:Epinephrine