2272-25-5

Usage

Chemical structure

Trisubstituted 1,3,5-triazine compound

Appearance

White, crystalline organic compound

Usage

Building block in organic synthesis

Application areas

Preparation of heterocyclic compounds and pharmaceuticals

Role in chemical reactions

Acts as a nucleophilic catalyst

Potential applications

Materials science and nanotechnology

Reagent classification

Versatile and valuable chemical reagent in organic chemistry

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 106-49-0 p-toluidine 
• 2515-30-2 6-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine 

Relevant academic research and scientific papers

Sterically enriched bulky 1,3-bis(: N, N ′-aralkyl)benzimidazolium based Pd-PEPPSI complexes for Buchwald-Hartwig amination reactions

Pd-PEPPSI (palladium-pyridine enhanced pre-catalyst preparation stabilization and initiation) complexes are now emerging as well-defined catalysts for C-C and C-N bond formation. In connection with this, we prepared a family of six air and moisture stable

Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship

A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent density functional theory (TD-DFT) [B3LYP/6–311 + G(d,p)]. A suitable forecasting model (R > 0.8, P 0.0001) was revealed. Predictive three-dimensional quantitative structure-property relationship (3D-QSPR) model was established using multifit molecular alignment rule of Sybyl program, which conclusion is consistent with the TD-DFT calculation. The exceptional photostability mechanism of such ultraviolet rays absorber compounds was studied and confirmed as principally banked upon their ability to undergo excited-state deactivation via an ultrafast excited-state proton transfer (ESIPT). The intramolecular hydrogen bond (IMHB) of 1,3,5-triazines compounds is the basis for the excited state proton transfer, which was explored by IR spectroscopy, UV spectra, structural and energetic aspects of different conformers and frontier molecular orbitals analysis.

Vibrational and optical characterization of s-triazine derivatives

The optical and electron properties of three different s-triazine derivatives are investigated to ascertain the role of the donor acceptor character in amine-triazine systems depending on the bridging radical of the ammine group. The three derivatives wer

Design, discovery, modelling, synthesis, and biological evaluation of novel and small, low toxicity s-triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors

A set of top-ranked compounds from a multi-objective in silico screen was experimentally tested for toxicity and the ability to inhibit the activity of HIV-1 reverse transcriptase (RT) in cell-free assay and in cell-based assay using HIV-1 based virus-like particles. Detailed analysis of a commercial sample that indicated specific inhibition of HIV-1 reverse transcription revealed that a minor component that was structurally similar to that of the main compound was responsible for the strongest inhibition. As a result, novel s-triazine derivatives were proposed, modelled, discovered, and synthesised, and their antiviral activity and cellular toxicity were tested. Compounds 18a and 18b were found to be efficient HIV-1 RT inhibitors, with an IC50 of 5.6 ± 1.1 μM and 0.16 ± 0.05 μM in a cell-based assay using infectious HIV-1, respectively. Compound 18b also had no detectable toxicity for different human cell lines. Their binding mode and interactions with the RT suggest that there was strong and adaptable binding in a tight (NNRTI) hydrophobic pocket. In summary, this iterative study produced structural clues and led to a group of non-toxic, novel compounds to inhibit HIV-RT with up to nanomolar potency.

An efficient, "green" approach to aryl amination of cyanuric chloride using acetic acid as solvent

(Chemical Equation Presented) Acetic acid is an inexpensive and environmentally friendly solvent for facile, clean and high-yielding aryl amination of cyanuric chloride with aromatic amines, including nitroanilines. Aryl animation in acetic acid medium and isolation protocol are greatly simplified as compared to previously reported procedures. Under proper conditions, it is possible to attach the same or different aniline residues in a controlled way to obtain in excellent yields symmetrical and unsymmetrical 1,3,5-triazine derivatives, respectively.

Microwave assisted synthesis of 2,4,6-triarylamino-1,3,5-triazines as potential UV absorbent

2,4,6-Triarylamino-1,3,5-triazines was synthesized in a few minutes by reaction of cyanuric chloride with aromatic amines under microwave irradiation. This method is featured with rapid reaction, convenient operation, high yield, and clean. UV-absorption was tested for each compound.