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Selective synthesis of polyamine derivatives: Efficient derivatization of the secondary amino group ofN-monosubstituted 1,3-diamines


Jentgens, Christian; Hofmann, Richard; Guggisberg, Armin; Bienz, Stefan; Hesse, Manfred (1997). Selective synthesis of polyamine derivatives: Efficient derivatization of the secondary amino group ofN-monosubstituted 1,3-diamines. Helvetica Chimica Acta, 80(3):966-978.

Abstract

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. N4,N9-bis[3-phenylprop-2-enoyl]spermine (4a), which was further converted to N',N'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.

Abstract

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. N4,N9-bis[3-phenylprop-2-enoyl]spermine (4a), which was further converted to N',N'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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1997
Deposited On:25 Aug 2017 13:38
Last Modified:20 Feb 2018 08:38
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/hlca.19970800328

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