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Synthesis 2003(13): 2015-2022
DOI: 10.1055/s-2003-41040
DOI: 10.1055/s-2003-41040
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Novel Access to 2-Aminofuranones via Cyclization of Functionalized γ-Hydroxy-α,β-butenoates Derived from N-Hydroxybenzotriazole Esters of α-Hydroxy Acids
Further Information
Received
24 February 2003
Publication Date:
28 August 2003 (online)
Publication History
Publication Date:
28 August 2003 (online)
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Abstract
The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of γ-hydroxy-functionalized butenoates which are cyclized under mild conditions to the corresponding 2-amino-3,5-disubstituted-4-furanones. That the products are optically active is confirmed by measurements of their optical rotations. On the other hand, replacement of N-hydroxybenzotriazole by N-hydroxysuccinimide might lead to by-products depending on the functionalized glycolic acid used.
Key words
acylations - furans - heterocycles - lactones - alkenes - carboxylic acids
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