This concept review describes the recent achievements on the Heyns rearrangement appeared in literature over the last decade and aims to provide the reader with a general overview of the fundamental synthetic advances in this research area.
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Reversal of Reactivity of Heyns Intermediate for the Concise Synthesis of Substituted 3-Hydroxyquinolines.
J Org Chem
November 2024
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
An efficient and general method for the synthesis of 3-hydroxyquinolines has been achieved from -acylanilines and α-hydroxyketones in good yields. The strategy involves the intramolecular reverse trapping of the generated aminoenol intermediate with an electrophilic carbonyl, . an interrupted Heyns rearrangement, followed by aromatization.
View Article and Find Full Text PDFDietary glycation compounds - implications for human health.
Crit Rev Toxicol
September 2024
Department of Toxicology, University of Würzburg, Würzburg, Germany.
The term "glycation compounds" comprises a wide range of structurally diverse compounds that are formed endogenously and in food the Maillard reaction, a chemical reaction between reducing sugars and amino acids. Glycation compounds produced endogenously are considered to contribute to a range of diseases. This has led to the hypothesis that glycation compounds present in food may also cause adverse effects and thus pose a nutritional risk to human health.
View Article and Find Full Text PDFRegioselective Synthesis of 2,3-Disubstituted Indoles via Interrupted Heyns Rearrangement Involving C-C Bond Cleavage.
Chem Asian J
November 2024
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
A novel metal free, Brønsted acid mediated and operationally simple strategy has been developed for regioselective synthesis of 2,3-disubstituted indoles from α-hydroxyketones and o-aminoaryl ketones in excellent yields. The reaction proceeds via interrupted Heyns rearrangement through the generation of aminoenol intermediate followed by intramolecular trapping and aromatization with C-C bond cleavage and release of corresponding ester. The mechanism was further supported by the identification of ester in GCMS and reaction of cyclic α-hydroxydimethylketal, which afforded ester tethered indole derivative.
View Article and Find Full Text PDFFormal One Carbon Deletion of Indoline Hemiaminals under Tautomeric Control to Access 2-Aminobenzyl Compounds.
J Org Chem
July 2024
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 7008530, Japan.
Unprecedented -BuOK-mediated one carbon deletion of indoline hemiaminals has been achieved. This novel protocol provides an efficient synthetic tool for the construction of 2-aminobenzyl compounds with high chemoselectivity. In addition, functionalized 2-aminobenzyl compounds are difficult to make, for which few limited means of access currently exist.
View Article and Find Full Text PDFAmadori and Heyns rearrangement products of bioactive peptides as potential new ligands of galectin-3.
Carbohydr Res
August 2024
Florida Atlantic University, Department of Chemistry and Biochemistry, 777 Glades Rd., Boca Raton, FL, 33431, USA. Electronic address:
Non-enzymatic cascade reactions between amines and reducing sugars are known as Maillard reaction. The late phase of these reactions consists of advanced glycation end products (AGEs), which have been implicated in the pathogenesis of numerous human diseases. Recent evidence suggests that galectin-3 acts as a receptor for AGEs and some early products of the Maillard reaction.
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