Stereoselective access to (Z)-α,γ-diazido-α,β-unsaturated esters via Lewis acid-mediated 1,3-diazidation of α,α-dimethoxy-β,γ-unsaturated esters with trimethylsilyl azide

Synthesis of 1,2,3-Triazines Using the Base-Mediated Cyclization of (Z)-2,4-Diazido-2-alkenoates

“…In previous work, we developed a synthetic method for accessing a new class of diazide compounds, ( Z )-2,4-diazido-2-alkenoates 1 , using 1,3-diazidation of 2,2-dimethoxy-3-alkenoates with 2.2 equiv of trimethylsilyl azide in the presence of Lewis acid . During our further exploration of the synthetic utility of the diazide compounds 1 , , we unexpectedly observed that 1,2,3-triazine 2 (R = Ph, R′ = Me) was generated by a simple treatment with Cs 2 CO 3 in DMF.…”