193968-43-3

Usage

Uses

Used in Catalyst Industry:
2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-diphenylis used as a chelating ligand for metal ions in metal-catalyzed reactions. Its ability to coordinate with metal ions enhances the efficiency and selectivity of these reactions, making it a valuable component in the development of new catalysts.
Used in Organic Synthesis:
In the field of organic synthesis, 2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-diphenylserves as a versatile building block for constructing complex molecules. Its unique structure and reactivity contribute to the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-diphenylhas been studied for its potential applications in medicinal chemistry. Its unique structure and properties make it a promising candidate for the development of new pharmaceuticals and biologically active compounds, with potential applications in various therapeutic areas.
Used in Drug Development:
In the pharmaceutical industry, 2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-diphenylis utilized in drug development as a key intermediate or scaffold for the synthesis of novel drug candidates. Its ability to form stable complexes with metal ions and its compatibility with various chemical reactions make it a valuable tool in the design and synthesis of innovative therapeutic agents.

Upstream product

• 1191-95-3 cyclobutanone 
• 100-47-0 benzonitrile 

Downstream Products

• 950603-96-0 4,5-Dimethylene-2,6-diphenyl-4,5-dihydro-pyrimidine 

Relevant academic research and scientific papers

Diels-Alder Cycloadducts of Fullerene with Pyrimidine o-Quinodimethanes

Novel organofullerenes bearing a pyrimidine nucleus covalently attached to the C60 cage have been prepared by cycloaddition reactions of C60 and pyrimidine o-quinodimethanes generated "in situ" from the readily available cyclobutapyrimidines which are prepared in a one-pot procedure from cyclobutanone and alkyl or aryl nitriles. The reaction mechanism involves formation of a nitrilium cation with participation of two molecules of the respective nitrile. A side-product (16) formed from two cyclobutanone molecules is obtained together with the target cyclobutapyrimidines 4a-d. Compounds 4a-d are appropriate precursors for the generation of substituted pyrimidine o-quinodimethanes 5a-d which are efficiently trapped by the C60 molecule in a cycloaddition reaction which according to theoretical calculations is controlled by the HOMO of the diene. 1H NMR spectra indicate the presence of a dynamic process attributed to the boat-to-boat interconversion of the cyclohexene ring. The activation free energy has been measured by dynamic NMR experiments showing values ΔG(act.) ca. 16-17 kcal/mol for both methylene groups, depending upon the substituents on the pyrimidine unit. Theoretical calculations at the semiempirical PM3 level confirm the presence of a boat conformation for the cyclohexene ring which undergoes a rapid flipping motion resulting in an average Cs symmetry as it is observed in the 1H NMR spectra. The cyclic voltammetry measurements show the presence of reduction waves cathodically shifted, related to C60, due to the saturation of a double bond of the C60 cage. A weak electronic interaction is observed between the pyrimidine moiety and the C60 core.

An expeditious procedure for the generation of pyrimidine ortho-quinodimethanes

The one step synthesis of 2,4-dialkyl and 2,4-diaryl substituted 5,6-dihydrocyclobuta[d]pyrimidines (12a,b) as new precursors for pyrimidine ortho-quinodimethanes and their trapping with different dienophiles and C60 is reported.