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Selective Synthesis of Polyamine Derivatives: Efficient derivatization of the secondary amino group of N ‐monosubstituted 1,3‐diamines
Author(s) -
Jentgens Christian,
Hofmann Richard,
Guggisberg Armin,
Bienz Stefan,
Hesse Manfred
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800328
Subject(s) - chemistry , yield (engineering) , derivatization , benzaldehyde , spermine , electrophile , hydrolysis , polyamine , formylation , medicinal chemistry , selectivity , nucleophile , organic chemistry , stereochemistry , high performance liquid chromatography , biochemistry , materials science , metallurgy , enzyme , catalysis
N ‐Monosubstituted 1,3‐diamines were selectively functionalized at the secondary N‐atom via 2‐Ph‐substituted hexahydropyrimidine intermediates. Reaction of the diamines with benzaldehyde, followed by treatment with an electrophile and hydrolysis, provided the desired products with excellent selectivity and in high yields. N 4 , N 9 ‐bis[3‐phenylprop‐2‐enoyl]spermine ( 4a ), which was further converted to N 1 , N 1 2 ‐bis[3‐phenylprop‐2‐enoyl]spermine ( 15 ) by a transamidation reaction, was prepared by this way in 82% yield from spermine ( 1 ). Compound 4a was alternatively synthesized in 83% yield, equally from 1 , by a sequence involving intermediary protection of the terminal amino groups.