Rational design of N-heterocyclic compound classes via regenerative cyclization of diamines.

Nat Commun

Lehrstuhl Anorganische Chemie II-Katalysatordesign, Sustainable Chemistry Centre, Universität Bayreuth, 95440, Bayreuth, Germany.

Published: February 2023

The discovery of reactions is a central topic in chemistry and especially interesting if access to compound classes, which have not yet been synthesized, is permitted. N-Heterocyclic compounds are very important due to their numerous applications in life and material science. We introduce here a consecutive three-component reaction, classes of N-heterocyclic compounds, and the associated synthesis concept (regenerative cyclisation). Our reaction starts with a diamine, which reacts with an amino alcohol via dehydrogenation, condensation, and cyclisation to form a new pair of amines that undergoes ring closure with an aldehyde, carbonyldiimidazole, or a dehydrogenated amino alcohol. Hydrogen is liberated in the first reaction step and the dehydrogenation catalyst used is based on manganese.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9898245PMC
http://dx.doi.org/10.1038/s41467-023-36220-wDOI Listing

Publication Analysis

Top Keywords

compound classes
8
n-heterocyclic compounds
8
amino alcohol
8
rational design
4
design n-heterocyclic
4
n-heterocyclic compound
4
classes regenerative
4
regenerative cyclization
4
cyclization diamines
4
diamines discovery
4

Similar Publications

Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study.

ACS Catal

October 2024

Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.

A class of generated Lewis acid (LA) activated acridine complexes is reported, which act as potent photochemical catalysts for the oxidation of a variety of protected secondary amines. Acridine/LA complexes exhibit tunable excited state reduction potentials ranging from +2.07 to 2.

View Article and Find Full Text PDF

Resorcinol-based Bolaamphiphilic Quaternary Ammonium Compounds.

ChemMedChem

January 2025

Villanova University, Chemistry, 800 E Lancaster Ave, 19085, Villanova, UNITED STATES OF AMERICA.

Quaternary ammonium compounds (QACs) play crucial disinfectant roles in healthcare, industry, and domestic settings. Most commercially utilized QACs like benzalkonium chloride have a common architectural theme, leading to a rise in bacterial resistance and urgent need for novel structural classes. Some potent QACs such as chlorhexidine (CHX) and octenidine (OCT) feature a bolaamphiphilic architecture, comprised of two cationic centers at the molecular periphery and a non-polar region connecting them; these compounds show promise to elude bacterial resistance mechanisms.

View Article and Find Full Text PDF

Halophytes display distinctive physiological mechanisms that enable their survival and growth under extreme saline conditions. This makes them potential candidates for their use in saline agriculture. In this research, tomato (Solanum lycopersium Mill.

View Article and Find Full Text PDF

Rationale: Extraterrestrial amines and ammonia are critical ingredients for the formation of astrobiologically important compounds such as amino acids and nucleobases. However, conventional methods for analyzing the composition and isotopic ratios of volatile amines suffer from lengthy derivatization and purification procedures, high sample mass consumption, and chromatographic interferences from derivatization reagents and non-target compounds.

Methods: Here we demonstrate a highly efficient method to analyze the composition and compound specific isotopic ratios of C to C amines as well as ammonia based on solid phase micro-extraction (SPME) on-fiber derivatization.

View Article and Find Full Text PDF

This investigation delves into the extraction of polyphenols from the flowers of Tabebuia rosea using a basic maceration approach with acetone, ethanol, and methanol as solvents. The spectroscopic analysis of the dye obtained confirms the existence of functional groups in the polyphenol extract. The study also explores optoelectronic, fluorescence, and photometric characteristics associated with polyphenols.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!