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Issue 11, 2018
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Bio-based triacetic acid lactone in the synthesis of azaheterocycles via a ring-opening transformation

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Abstract

In the present article a new way of converting bio-based triacetic acid lactone (TAL) into azaheterocyclic compounds, such as 4-pyridones, pyrazoles, isoxazolines and isoxazoles, has been found. The main strategy involves the transformation of TAL into reactive and multifunctional polycarbonyl intermediates serving as C-6 building blocks for the construction of organic compounds. TAL undergoes a ring opening transformation with aliphatic and aromatic amines, including bioavailable amines, under solvent free conditions or in EtOH to give carbamoylated enaminones (40–98%). These polyfunctional compounds have been converted into biologically important pyridone-3-carboxamides (91–99%) with dimethylformamide dimethyl acetal and also react regioselectively with hydrazines and hydroxylamine to form pyrazolyl- (72–96%) and (isoxazolinyl)acetoamides (60–91%). The conversion of TAL into hetarylacetic acid amides can be performed as one-pot reactions without isolation of polycarbonyl intermediates.

Graphical abstract: Bio-based triacetic acid lactone in the synthesis of azaheterocycles via a ring-opening transformation

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Publication details

The article was received on 03 Mar 2018, accepted on 15 Apr 2018 and first published on 16 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ01044G
Citation: New J. Chem., 2018,42, 8943-8952
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    Bio-based triacetic acid lactone in the synthesis of azaheterocycles via a ring-opening transformation

    D. L. Obydennov, A. I. El-Tantawy and V. Ya. Sosnovskikh, New J. Chem., 2018, 42, 8943
    DOI: 10.1039/C8NJ01044G

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