Photochemische Synthesen potentiell hypoglykämisch wirkender 3‐Oxazoline

Photochemical Syntheses of 3‐Oxazolines which Possibly Exhibit Hypoglycemic Activity Reactions of photochemically generated benzonitrile methylides 2 with carbonyl compounds 3 yielded 3‐oxazolines of the types 5 and 6 (Scheme 1). Photooxidation of 5‐[p‐(dimethylamino)phenyl]‐2,2‐dimethyl‐4‐phenyl‐3‐oxazoline (5a) gave 4′‐(2,2‐dimethyl‐4‐phenyl‐3‐oxazolin‐5‐yl)‐N‐methylformanilide (6r) which could be transformed to 2,2‐dimethyl‐5‐[p‐(methylamino)phenyl]‐4‐phenyl‐3‐oxazoline (6s) by photodecarbonylation. Thirty 3‐oxazolines of types 5 and 6 have been synthesized and tested by oral and/or intraperitoneal administration to starved rats and obese‐hyperglycemic mice.