Abstract
Various 1,3,5-triazines with electron-withdrawing groups such as esters, thioesters, and amides were prepared. These triazines were synthesized using acyl chloride coupling methods from triazine 1a and various alcohols, ethanethiol, and amines. Lowest unoccupied molecular orbital (LUMO) energy and solubility for these 1,3,5-triazines were determined to assess their potential as azadienes in inverse-electron-demand Diels–Alder reactions (IDA). The thioester 8 showed less LUMO energy and more solubility than triazine 1, suggesting that it may be a better azadiene to study triazine IDA reactions.
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