ScienceAsia 27 (2001) : 121-125 |doi: 10.2306/scienceasia1513-1874.2001.27.121

Solid Phase Synthesis of Substituted 4-Amino-5-Hydroxy-2(5H)-furanones

Pornthip Arayarat^a, Harjit Singh^b and Eric Lattmann^b,*

ABSTRACT: A solid phase approach towards the synthesis of substituted 4-amino-5-hydroxy-2(5H)- furanones was developed and applied to the construction of a two dimensional library of delta-2-butenolides. Four halogenated 5-hydroxy-delta-2-butenolide building blocks 1A-1D have been attached, via the 5-hydroxy group, to a scavenger isocyanate resin giving the resin bound carbamates 2A-2D. Reacting each resin bound butenolide 2A-2D individually with a total of 16 amines a-p furnished the 64 linked 4-amino-5-hydroxy-butenolides 3Aa-3Dp. After the cleavage from the resin with TFA 48 different and individual 4-alkylamino-5-hydroxy-2(5H)-furanones Aa-Cp were obtained from a total library of 64 compounds, as building block C and D resulted in the same molecules.

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a Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
b Aston University, Pharmaceutical Sciences Research Institute, Birmingham B4 7ET, UK.

* Corresponding author, E-mail: e.lattmann@aston.ac.uk

Received 7 Sep 2000, Accepted 30 Mar 2001