Synthesis of N-(2-aminoethyl)- and N-(3-aminopropyl)cytisine

Autor:	N. M. Vlasova, V. A. Dokichev, Leonid V. Spirikhin, Alexander N. Lobov, N. Z. Baibulatova, D. V. Shishkin
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Aqueous solution Chemistry Side reaction Plant Science General Chemistry Medicinal chemistry Aldehyde General Biochemistry Genetics and Molecular Biology chemistry.chemical_compound Cytisine Polymerization Yield (chemistry) Diamine Amide Organic chemistry
Zdroj:	Chemistry of Natural Compounds. 48:436-439
ISSN:	1573-8388 0009-3130
Popis:	Treatment of 2a or 2b with aqueous NH 4 OH in the presence of NH 4 Cl at 20–22°C produced in 4 h amides 3a and 3b in 80% yields. Reduction of 3a or 3b by a 12-fold molar excess of (i-Bu) 2 AlH in refluxing CH 2 Cl 2 gave in 2 h N-(2-aminoethyl)cytisine (4a) or N-(3-aminopropyl)cytisine (4b) in 15 and 98% yields, respectively. The low yield of 4a compared with 4b was probably related to polymerization of the reaction mixture as a result of a side reaction forming an aldehyde because of the high electrophilicity of the carbonyl in 3a. The reduction of 3b was used as an example to show that the yield of desired diamine 4b decreased to 90% if a 10:1 (i-Bu) 2 AlH:amide mole ratio was used. The yield of 4b was
Databáze:	OpenAIRE
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