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Title: A divergent synthesis of substituted 2-aminoimidazoles from 2-aminopyrimidines
Authors: Ermolat'ev, Denis S ×
Van der Eycken, Erik #
Issue Date: Sep-2008
Publisher: Amer chemical soc
Series Title: Journal of Organic Chemistry vol:73 issue:17 pages:6691-6697
Abstract: A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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