A Novel Access to 2-Aminofuranones via Cyclization of Functionalized γ-Hydroxy-α,β-butenoates Derived from N-Hydroxybenzotriazole Esters of α-Hydroxy Acids

Giorgos Athanasellis; Anastasia Detsi; Kyriakos Prousis; Olga Igglessi- Markopoulou; John Markopoulos

doi:10.1055/s-2003-41040

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Synthesis 2003(13): 2015-2022
DOI: 10.1055/s-2003-41040

PAPER

A Novel Access to 2-Aminofuranones via Cyclization of Functionalized γ-Hydroxy-α,β-butenoates Derived from N-Hydroxybenzotriazole Esters of α-Hydroxy Acids

Giorgos Athanasellis^a, Anastasia Detsi^a, Kyriakos Prousis^a, Olga Igglessi- Markopoulou*^a, John Markopoulos^b
^a Laboratory of Organic Chemistry, Department of Chemical Engineering, National Technical University of Athens, Zografou Campus, 15773 Athens, Greece
Fax: +3(210)7723072; e-Mail: ojmark@orfeas.chemeng.ntua.gr;
^b Laboratory of Inorganic Chemistry, Department of Chemistry, University of Athens, Athens, Greece

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Publication History

Received 24 February 2003
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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