Cinnamic acid, «-cyano-0-methyl

Cinnamic acid, a-cyano-/3-methyl-, ethyl ester)... 

Scheme 2 shows Rapoport s synthesis [15]. The cinnamic acid derivative 3 prepared from m-methoxy benzaldehyde [20] was ethylated by diethyl sulfate to give ethyl cinnamate derivative 4, followed by Michael addition with ethyl cyanoacetate to afford compound 5. Compound 5 was converted to lactam 6 by the reduction of the cyano group and subsequent cyclization. Selective reduction of the lactam moiety of 6 was achieved by treatment with trimethy-loxonium fluorob orate followed by sodium borohydride reduction. Amine 8 was obtained by the reductive methylation of amine 7. Amine 8 was converted to compound 9 by methylene lactam rearrangement [21], followed by selenium dioxide oxidation to provide compound 10. Allylic rearrangement of compound 10 and subsequent hydrolysis gave compound 12. The construction of the decahydroisoquinoline structure began with compound 12,... 

Substituted benzaldehydes and malonic acid give cinnamic acids in excellent yields. Among the common nuclear substituents are methyl, halo, " hydroxyl, methoxyl, " cyano, nitro, and diethylamino groups. Other /fi-arylacrylic acids have been made by the use of a-naphthaldehyde, phenanthraldehydes, and furfural. Phenyl-substituted aliphatic aldehydes have also been used in this condensation. ... 

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