193968-42-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-dimethyl(9CI) is used as a ligand in coordination chemistry for the stabilization of transition metal complexes, which is crucial in the development of pharmaceutical compounds.
Used in Organic Synthesis:
2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-dimethyl(9CI) serves as a building block in the synthesis of various organic compounds, contributing to the creation of a wide range of chemical products.
Used in Catalysis:
2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-dimethyl(9CI) is employed in catalytic processes, enhancing the efficiency of chemical reactions in various industries.
Used in Material Science:
2,4-Diazabicyclo[4.2.0]octa-1,3,5-triene, 3,5-dimethyl(9CI) has been studied for its potential use in the development of new materials, indicating its importance in advancing material science and technology.

Upstream product

• 1191-95-3 cyclobutanone 
• 75-05-8 acetonitrile 

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.