Work

Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids

Year: 2024

Type: article

Abstract: For the first time, recyclization of allomaltol derivatives with an amide fragment in the side chain were investigated. It was shown that the studied process leads to substituted tetronic acids bearing a pyrrolidinone moiety. The application of 1,1′-carbonyldiimidazole and DBU is necessary for implementation of the considered reaction. Based on the performed research a general method for the synthesis of a wide range of (3 E ,5 E )-3-(1-hydroxyethylidene)-5-(5-oxopyrrolidin-2-ylidene)furan-2,4(3 H ,5 H )-diones was elaborated. The advantages of the presented protocol are easily available starting compounds and simple isolation of the target products without chromatographic purification. The synthetic utility of the prepared tetronic acids was demonstrated by further transformations at the hydroxyethylidene fragment. The structures of one obtained tetronic acid and one product of derivatization were confirmed by X-ray analysis.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.20.217

Authors: Andrey Nikolaevich Komogortsev, Constantine Vyacheslavovich Milyutin, Boris Valerievich Lichitsky

Institutions: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Responsible consumption and production

Open Access status: diamond

OpenAlex ID: W4403380023