[Lactones. 22. Synthesis and reduction of alpha-aminomethylene-delta,delta-diphenyl-delta-valerolactones].
Treatment with tris-(dimethylamino)-methane resp. formylation and reaction with piperidine transfer 1 to 5a,b, which can not be reduced to the corresponding alpha-aminomethyllactones 4a,b, in contrast to the homologue 6 and other alpha-aminomethylene-gamma- and delta-lactones. Isolation of products and gc/ms-investigations verify the reaction course: The aminomethyl moiety in alpha-position of delta,delta-diarylated delta-lactones is instable and eliminates amine to give 7 (NaCNBH3) or 9 (H2/Pt). Only cleavage of the lactone ring enables the formation of stable aminomethyl compounds (10,11). 5a shows weak parasympatholytic and no H1-antihistaminic activity at the isolated guinea-pig ileum.
Lehmann
J
J
Institut für Pharmazeutische Chemie, Universität Hamburg.
Neugebauer
M
M
Marquardt
N
N
D000818:Animals; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D006168:Guinea Pigs; D006634:Histamine H1 Antagonists / Q000138:chemical synthesis*; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D009130:Muscle, Smooth / Q000187:drug effects*; D010276:Parasympatholytics / Q000138:chemical synthesis*
D001713:Biphenyl Compounds; D006634:Histamine H1 Antagonists; D007783:Lactones; D010276:Parasympatholytics
Lactone, 22. Mitt.: Zur Synthese und Reduktion von alpha-Aminomethylen-delta,delta-diphenyl-delta-valerolactonen.