A novel access to 2-aminofuranones via cyclization of functionalized gamma-hydroxy-alpha,beta-butenoates derived from N-hydroxybenzotriazole esters of alpha-hydroxy acids

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Title

A novel access to 2-aminofuranones via cyclization of functionalized gamma-hydroxy-alpha,beta-butenoates derived from N-hydroxybenzotriazole esters of alpha-hydroxy acids (EN)

Creator

Prousis, K (EN)

Markopoulos, J (EN)

Detsi, A (EN)

Igglessi-Markopoulou, O (EN)

Athanasellis, G (EN)

Type

journalArticle (EN)

Partial document
Publication in journal (EN)

Article
Scientific article (EN)

Issued

2014-03-01T01:53:05Z

2003 (EN)

Year

2003 (EN)

Description

The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of gamma-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. (EN)

Scientific field

Chemistry, Organic (EN)

Natural Sciences ▶ Chemical sciences
Organic Chemistry (EN)

Subject

lactones (EN)

heterocycles (EN)

acylations (EN)

furans (EN)

carboxylic acids (EN)

alkenes (EN)

DERIVATIVES (EN)

Journal