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Functionalization of Indoles with 1,3,5-Triazinanes: Chemistry of Aminomethylation vs the Hofmann-Martius-Type Rearrangement.
J Org Chem
January 2025
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India.
We have developed efficacious routes toward the selective synthesis of two classes of compounds such as C-3 amino-methylated indoles and 4-indol-3-yl-methylanilines from the same precursors, namely, indoles and 1,3,5-triazinanes. It is reported that the controlled cleavage of 1,3,5-triazinanes can be effected by heat for the generation of aryl imine motifs, and we observed that the presence of Lewis acid influences the course of these transformations toward different products. The reaction toward indol-3-yl-methylanilines proceeds via a nucleophilic attack of indole to the aryl imine generated from the 1,3,5-triazinanes to form an amino-methylated product which undergoes a Lewis acid mediated Hofmann-Martius-type rearrangement.
View Article and Find Full Text PDFSynthesis of nonaromatic [16]thiatriphyrin(2.2.1)s.
Org Biomol Chem
January 2025
Department of Chemistry, IIT Bombay, Powai, Mumbai 400076, India.
[16]Thiatriphyrin(2.2.1)s containing one thiophene and two pyrroles connected five -carbons were synthesized by condensing a new precursor, -fused thiatripyrrane, with an appropriate aryl aldehyde in CHCl under acid-catalyzed inert conditions followed by open air oxidation with DDQ.
View Article and Find Full Text PDFRecent Advances in Direct Synthesis of Functional Polymers of Intrinsic Microporosity Based on (Super)Acid Catalysis.
Macromol Rapid Commun
January 2025
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China.
Polymers of intrinsic microporosity (PIMs) are an emerging class of amorphous organic porous materials with solution processability, which are widely used in a multitude of fields such as gas separation, ion conduction, nanofiltration, etc. PIMs have adjustable pore structure and functional pore wall, so it can achieve selective sieving for specific substances. In order to meet the functional requirements of PIMs, two principal methods are used to synthesize functional PIMs, namely, post-modification of PIMs precursors and functionalization of monomers.
View Article and Find Full Text PDFAcid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines.
Molecules
January 2025
School of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, China.
In this study, we present the HOAc-catalyzed selective cleavage of the C=C double bond of enaminones, enabling the formation of a new C-N bond and a new C=N bond for the one-pot synthesis of 2-substituted 3,4-dihydroquinazolines directly from ynones and 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free and oxidant-free conditions, offering a sustainable and efficient approach for the synthesis of 3,4-dihydroquinazolines with broad functional group tolerance.
View Article and Find Full Text PDFAcid-catalyzed conversion of sesamolin to sesamol: Kinetics and reaction mechanism based on density functional theory.
Food Chem
January 2025
College of Food Science and Engineering, Henan University of Technology, Zhengzhou 450001, China. Electronic address:
Sesamol is a significant lignan in sesame oil, which can be converted from sesamolin under acid-catalyzed conditions. The effects of several factors on the conversion of sesamolin to sesamol under acid-catalyzed conditions were investigated. The conversion kinetics were studied and the relevant conversion mechanism was revealed by density functional theory (DFT).
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