Cinnamic acid amides

EXTENSIONS AND COMMENTARY There are about twenty different synthetic routes in the literature for the preparation of MDA. Many start with piperonal, and employ it to make methylenedioxyphenylacetone or a mcthylcnedioxydihydro-cinnamic acid amide instead of the nitrostyrene. The phenylacetone can be reduced in several ways other than the cyanoborohydride method mentioned here, and the amide can be rearranged directly to MDA. And there are additional methods for the reduction of the nitrostyrene that use no lithium aluminum hydride. Also there are procedures that have safrole or isosafrole as starting points. There is even one in the underground literature that starts with sassafras root bark. In fact, it is because safrole is one of the ten essential oils that MDA can humorously be referred to as one of the Ten Essential Amphetamines. See the comments under TMA. 

In a similar approach, a pretuned glass encased microchip set to emit a unique binary code is placed in a polypropylene tea bag loaded with polystyrene beads. Using a modified split synthesis approach, a 125-membered tripeptide library N-capped as the /r-carboxy-cinnamic acid amide was prepared on Rink resin. Each porous reactor contained a radio frequency transporter which successfully defined the structure of two inhibitors of protein tyrosine phosphatase [37],... 

Various unclassified alkaloids (aniline and anthranilic acid derivatives, cinnamic acid amides, guanidine bases, and oxazoles) are briefly reviewed in a general text on alkaloids.30... 

Hagel,J.M. and P.J.Facchini Elevated tyrosine decarboxylase and tyramine hydroxycinnamoyltransferase levels increase wound-induced tyramine-derived hydroxy-cinnamic acid amide accumulation in transgenic tobacco leaves Planta 221 (2005) 904-914. 

Tanguy, J.M., F. Cabanne, E. Perdrizet, and C. Martin The distribution of hydroxy cinnamic acid amides in flowering plants Phytochemistry 17 (1978) 1927-1928. 

EXTENSIONS AND COMMENTARY There are about twenty different synthetic routes in the literature for the preparation of MDA. Many start with piperonal, and employ it to make methylenedioxyphenylacetone or a methylenedioxydihydro-cinnamic acid amide instead of the nitrostyrene. The phenylacetone can be reduced in several ways other than the... 

In roasted cocoa powders, 13 Cinnamic acid amides [48-50] have been quantified, which are also found in fresh seeds, but unfortunately there are no quantitative data for these amides in unprocessed fresh cacao seeds ... 

Fig. 52.1 Cinnamic acid amides (a) Caffeoyl-L-DOPA = clovamid, (b) Caffeoyl-L-aspartate...

Hydroxybenzyl alcohol, 2888 6-Hydroxycaespitol, 2892 Hydroxycinnamates, 1549 Hydroxy cinnamic acid amides, 1604 Hydroxycinnamic acids, 1953, 2346, 2589 Hydroxycitronellal, 2999... 

As the only general method for this transformation at present is catalytic hydrogenation, the potential of this procedure is obvious. Appropriate N-methyl-a,j8-unsaturated amides undergo /3 -metallation on treatment with Bu Li-TMEDA to provide dianions (e.g. 214), which are useful for the further homologation of these molecules. (Z)-Cinnamic acid amides (216), which are not easy to prepare, have been obtained by rearrangement of anions (215) that themselves are derived from the [Stt + 2-n-] adducts formed between azahep-tafulvenes and monosubstituted ketens. ... 

A range of substituted cinnamic acid amides are found to undergo cycH-zation under high-temperature FVP conditions to afford the corresponding pyrrohdinones. The reaction was initially described for N,N-dimethyl amides... 

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