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.

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    Methyl 2(6)-nitro-3-methoxy-4:5-methylenedioxycinnamate is readily- reduced to the corresponding amino-compound, which, in the presence ch2<0 CHO — CH,< 0 CHO Ol jNOr —^ OMe (V.) OMe (VI.) ch2<0 ch:ch*co9h no9 OMe (VII.) of acids, is transformed into 2-keto-8(5)-methoxy-6 : 7-methylenedioxy- 1 : 2-dihydroquinoline (VIII). CH2< Or ,CH:CH*COoMe ^TT- xCH:CH-C0oMe O' JNO, __>CH2< 0 Nil —> OMe OMe 0 ch9<0 XCH :ch nh-co OMe (VIII.) 2-Keto - 8(5)- methoxy-6 : 7-methylenedioxy- 1:2- dihydroquinoline is of considerable interest on account of its relationship to eotarnine (X). If the formulae of the two substances are compared, it would appear possible to convert the former by reduction and methylation into an isomeride of eotarnine, which might appropriately be designated isocotarnine (IX). cn2<y> :(rH 2 (\//XH-CO 2 °\//XMe*CH-OH OMe OMe (VIII.) (IX.) CH <-'0'/XiCH2-9H2 2<^°\/CH(OH)-NMe OMe (X.) 2-Keto-8(5)-methoxy-6 :7-methylenedioxy-l: 2-dihydroquinoline, how¬ ever, polymerises so easily on reduction, either in acid or in alkaline solution, that it was found impossible to prepare the unimolecular reduction product. In this respect its behaviour is similar to that of carbostyril itself towards reducing agents, as Friedlander and Muller (Her., 1887, 20, 2012) have shown. In order to avoid this polymerisa¬ tion, 2-keto-8(5)-methoxy-6 : 7-methylenedioxy-1 : 2-dihydroquinoline