By Inc. BarCharts
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Extra resources for BarCharts QuickStudy Chemistry Equations & Answers
Example text
EtO HO ~N) ~NJ NH 2 (HO=EtO) MgI y I EtMgI H NH 2 -----+ Mel ~N) ~;S) Me Me HO~ EtO~ (hypotheticaO.... ~ Me Me eseroline HO~ ~N~~) Me 34 INDOLE ALKALOIDS Me ~ N Me 0 Me NH 2 EtOCCb Me Et0Ct:t' ~ N~O NH Me P20S Na/EtOH > ? H~el dl-eserethole Me N N Me N ~ N Me 0.. J eserethole methiodide Me Ie ~ --+ Me ~N~O Et00--YEt Me Me Htl1 ~ 2. Hofmann 3. H I. Mel N Me 2 HOG --+ Me N/ ~O Me NMe2 K3 Fe (CN)6 NMe2 OH eserethole methine N Me Me 37 SIMPLE DERIVATIVES OF TRYPTOPHAN NMe, The Harmala Bases. Harmine (the main base), harmahne and harmalol, along with the quinazoUne, vasicine, make u p about 2 - 3 % of the seeds of the rutaceous plant, Peganum harmala.
Pyrolysis of isoevodiamine hydrochloride evolved water, methyl chloride and by oxidation or disproportionation yielded rutaecarpine. Oxidation of evodiamine with potassium permanganate in acetone gave hydroxyevodiamine (a misnomer since it is a fcw-amide). Boiling these derivatives in alcoholic potassium hydroxide furnished j3-carboUne, tryptamine and anthranilic acid derivatives. 3. The synthetic approaches are for the large part reversals of the degradative steps but in an interesting variant o-aminobenzaldehyde was first coupled to 3,4-dihydro-j8-carbohne then oxidized.
5. The double bond must in some way facilitate the racemization of lysergic acid ^/-lysergic acid b u t n o t dihydrolysergic acid is racemized by heating it in baryta at ISO"" under nitrogen). 6). 6. If lysergic acid is pyrolysed fission typical of a jS-amino acid is observed resulting in a n unsaturated lactam. All doubts as t o the correctness of the structure of lysergic acid were removed by a synthesis first of all of rú[c-6,8-dimethylergoline and then rac-dihydrolysergic acid but the comparisons were made difficult because of the production of isomers (three asymmetric centres are involved).