A traceless solid-phase synthesis of 2-imidazolones

A traceless solid-phase synthesis of 2-imidazolones has been developed. Polymer-bound glycerol resin was reacted with bromoacetaldehyde diethyl acetal to give the cyclic acetal bromide on the solid support. Amination of the resin-bound acetal bromide followed by urea formation by reaction with isocy...

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Bibliographic Details
Published in:Tetrahedron letters 2002-06, Vol.43 (26), p.4571-4573
Main Authors: Cheng, Jie-Fei, Kaiho, Christopher, Chen, Mi, Arrhenius, Thomas, Nadzan, Alex
Format: Article
Language:English
Subjects:
2-imidazolone
solid-phase organic synthesis
traceless linker
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Summary:A traceless solid-phase synthesis of 2-imidazolones has been developed. Polymer-bound glycerol resin was reacted with bromoacetaldehyde diethyl acetal to give the cyclic acetal bromide on the solid support. Amination of the resin-bound acetal bromide followed by urea formation by reaction with isocyanates afforded the resin-bound urea acetals. The aldehyde urea intermediate, which was released from the resin upon treatment with TFA, immediately cyclized to afford the desired 2-imidazolones in good yield and purity. Resin-bound acetal amines ( 3 ) that are formed via amination of the bromide precursor are reacted with isocyanates to give the urea acetals ( 4 ), which upon treatment with TFA afford 2-imidazolones ( 5 ) in good yield and purity.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)00897-3