The synthesis of substances allied to cotarnine / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1909?]
Catalogue details

Licence: In copyright

Credit: The synthesis of substances allied to cotarnine / by Arthur H. Salway. Source: Wellcome Collection.

    4/22 page 1205
    a convenient starting-point for the synthesis of cotarnine, the constitution of which has been the subject of considerable discussion. Roser (Annctlen, 1888, 249, 156), on the one hand, in consideration of the fact that cotarnine behaves both as an aldehyde and a secondary amine, assigns to it the formula (I), whilst its hydrochloride, which is formed with elimination of the elements of water, is given the formula (II). Decker (J. pv. Chem., 1893, [ii], 47, 222), on the other hand, draws attention to the improbability of the co-existence of an aldehydic residue and a secondary amino-group in the same molecule, and points out that Roser’s formula does not explain why cotarnine is precipitated from its hydrochloride in the aldehydic form, or why hydrocotarnine (III) is converted into cotarnine on oxidation. For these reasons, Decker proposes formula (IV). r.u /0/\cH,-CHo-NHMe ch*N>In !ch0 - OMe OMe (III.) OMe (II.) ch ^°r 2N)^/jCH(OH)*lSTMe- OMe (IV.) With the object of effecting the synthesis of cotarnine from myristicin, the first experiments consisted in preparing methoxy- methylenedioxy-a-hydrindone, which was obtained according to the- following scheme of reactions : CH2<£| j CHO OMe Myristicinaldehyde. —> ch2<£ ch:ch-co2h OMe 3-Methoxy-4 : 5-methvlenedioxy- cinnamic acid. OMe Methoxymethylenedioxy-a- hydrindone. * 2 CH <0|/N10H.-Cj=,-C°sH °\/ OMe /3-3-Methoxy-4 : 5-methylenedioxy- phenylpropionic acid. Of the two possible formulae for methoxymethylenedioxy-a-liydrindone, namely r OMe ch2<q| n1co->oh» and CH2<ol Jco->ch”-’ OMe ' ^ Lhe former has been adopted throughout this communication. The same applies to
    digitised image 1
    digitised image 2
    digitised image 3