The synthesis of -heterocycles composes a significant part of synthetic chemistry. In this report, a Cu(II)-catalyzed green and efficient synthesis of pyrrolo[1,2-]quinoxaline, quinazolin-4-one, and benzo[4,5]imidazoquinazoline derivatives was developed, employing -dimethylethanolamine (DMEA) as a C1 synthon. Green oxidant O is critical in these transformations, facilitating the formation of a key intermediate─a reactive iminium ion. The method conducted under mild conditions is compatible with a diversity of functional groups, providing an appealing alternative to the previously developed protocols.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.2c02079DOI Listing

Publication Analysis

Top Keywords

application -dimethylethanolamine
4
-dimethylethanolamine one-carbon
4
one-carbon synthon
4
synthon synthesis
4
synthesis pyrrolo[12-]quinoxalines
4
pyrrolo[12-]quinoxalines quinazolin-4-ones
4
quinazolin-4-ones benzo[45]imidazoquinazolines
4
benzo[45]imidazoquinazolines annulation
4
annulation synthesis
4
synthesis -heterocycles
4

Similar Publications

Background: Bacterial vaginosis (BV) is a common clinical manifestation of a perturbed vaginal ecology associated with adverse sexual and reproductive health outcomes if left untreated. The existing diagnostic modalities are either cumbersome or require skilled expertise, warranting alternate tests. Application of machine-learning tools to heterogeneous and high-dimensional multi-omics datasets finds promising potential in data integration and may aid biomarker discovery.

View Article and Find Full Text PDF

2-(Dimethylamino)ethan-1-ol (Deanol) is a widely produced chemical used by both industry and consumers in a variety of applications. Meclofenoxate, a stimulant classified on the World Anti-Doping Agency Prohibited List, metabolizes into deanol and, presumably, its main metabolite deanol-N-oxide. Hence, using liquid chromatography-tandem mass spectrometry, a quantitative detection method for deanol-N-oxide in urine was developed.

View Article and Find Full Text PDF

The benzylation of three low molecular weight N,N-disubstituted ethanolamines related to chemical warfare agents (CWAs) to furnish derivatives with improved gas chromatography-mass spectrometry (GC-MS) profiles is described. Due to their low molecular weight and polar nature, N,N-disubstituted ethanolamines are notoriously difficult to detect by routine GC-MS analyses during Organisation for the Prohibition of Chemical Weapons (OPCW) proficiency tests (PTs), particularly in scenarios when they are present at low levels (~1-10 ppm) amidst more abundant interferences. Our studies revealed that the optimal derivatization conditions involved the treatment of the ethanolamine with benzyl bromide in the presence of an inorganic base (e.

View Article and Find Full Text PDF

The synthesis of -heterocycles composes a significant part of synthetic chemistry. In this report, a Cu(II)-catalyzed green and efficient synthesis of pyrrolo[1,2-]quinoxaline, quinazolin-4-one, and benzo[4,5]imidazoquinazoline derivatives was developed, employing -dimethylethanolamine (DMEA) as a C1 synthon. Green oxidant O is critical in these transformations, facilitating the formation of a key intermediate─a reactive iminium ion.

View Article and Find Full Text PDF

A Greener Route to Blue: Solid-State Synthesis of Phthalocyanines.

Angew Chem Int Ed Engl

October 2022

Department of Bioproducts and Biosystems, Aalto University, 02150, Espoo, Finland.

Phthalocyanines are important organic dyes with a broad applicability in optoelectronics, catalysis, sensing and nanomedicine. Currently, phthalocyanines are synthetized in high boiling organic solvents, like dimethylaminoethanol (DMAE), which is a flammable, corrosive, and bioactive substance, miscible with water and harmful to the environment. Here we show a new solid-state approach for the high-yielding synthesis of phthalocyanines, which reduces up to 100-fold the amount of DMAE.

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!