[Medium sized rings from alprenolol and oxprenolol].
The N-allyl derivatives 2 formed from the beta-blockers 1, were acetylated to give the esters 5. The 1,5-benzoxazacycloundecine 6a and the 1,10,5-benzodioxazacyclododecine 7a were isolated by ring closing metathesis (RCM) of 5a and 5b, respectively, using Grubbs catalyst in the presence of titanium tetraisopropanolate. Alkaline hydrolysis yielded the alcohols 6b and 7b.
Görlitzer
K
K
Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Lorenz
A
A
D000107:Acetylation; D000319:Adrenergic beta-Antagonists / Q000737:chemistry*; D000526:Alprenolol / Q000737:chemistry*; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010096:Oxprenolol / Q000737:chemistry*; D014025:Titanium
D000319:Adrenergic beta-Antagonists; D007202:Indicators and Reagents; D010096:Oxprenolol; D000526:Alprenolol; D014025:Titanium