Issue 11, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
03 Mar 2018
Accepted
15 Apr 2018
First published
16 Apr 2018

New J. Chem., 2018,42, 8943-8952

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements