~Current Project~
Synthesis of a New 1,2,4-Triazoline-3,5-dione and Assessment of its Reactivity
N-R-1,2,4-Triazoline-3,5-diones (RTADs) are highly electrophilic azo compounds (i.e., compounds with the N=N bond) where R can be alkyl or phenyl groups.
Two of the most commonly used RTADs have R = Me and R = Ph
TADs engage in a variety of reactions that afford products of a diverse nature that can be difficult to synthesize by other methods such as aryl hydrazines, 1,2-diazetidines and diazaheterocycles
Of the two commonly used TAD compounds, PhTAD is the more reactive.
However, MeTAD is a more convenient to use TAD because the N-Me signal is characteristic in the 1H NMR spectrum at ~ 3 ppm, is a simple singlet, and makes it easy to track reactions simply by following changes in the N-Me signal.
The benzene ring of PhTAD does not provide nearly a clear indicator as to the extent of reaction or the potential number of products formed due to overlap of the complicated signals.
Although MeTAD is convenient, it is no longer commercially available because it requires the use of a highly toxic compound (methyl isocyanate) in its traditional synthesis.
We are interested in synthesizing a new derivative of RTAD where R = OMe (see below) with the hope that it will combine the high reactivity of PhTAD with the convenient simple singlet of the methyl group of MeTAD.
We are currently working on the synthesis of this compound and this will be followed by testing its reactivity against those of MeTAD and PhTAD.
