16055-19-9Relevant academic research and scientific papers
The aza-xylylene Diels-Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines
Avemaria, Frank,Vanderheiden, Sylvia,Br?se, Stefan
, p. 6785 - 6796 (2007/10/03)
The recently discovered intramolecular aza-xylylene Diels-Alder reaction, based on a 1,4-dehydrohalogenation reaction, was extended in terms of substrates and leaving groups allowing the assembly of tetrahydroquinolines in two synthetic steps. Intramolecular cleavage of a thiocarbamate using triphenylphosphine and tetrachloromethane (Appel conditions) to give chloromethyl phenylisocyanate has been presented for the first time. The synthetic feasibility of this process was demonstrated in the first total syntheses of the alkaloids rac-Angustureine and 1-methyl-2-propyltetrahydroquinoline.
207. Photo-Emde Degradation of 1,2,3,4-Tetrahydroquinolinium Salts
Partali, Vassilia,Jolidon, Synese,Hansen, Hans-Juergen
, p. 1952 - 1960 (2007/10/02)
It is shown that 1,1-dimethyl-1,2,3,4-tetrahydroquinolinium ions undergo, under direct irradiation through quartz in CH3OH and independent of the nature of the counterion (I-, BF4-), a reductive cleavage of the N(1)-C(8a) bond (photo-Emde degradation).The corresponding N,N-dimethyl-3-phenylpropylamines are formed in high yields and without contamination by Hofmann degradation products of the tetrahydroquinolinium salts.Me groups at C(2) as well as substituents at C(6) (CH3, Cl, CH3O) favour the photo-Emde degradation.The aromatic Cl-substituent is reductively split off in the course of the photoreaction.
