Synthesis of Electron-Deficient 1, 3, 5-Triazines as Potential Azadienes for Inverse-Electron-Demand Diels–Alder Reactions

…, L Zheng, S Wang, Q Dang, X Bai

Index: Xu, Guoxing; Zheng, Lianyou; Wang, Shixue; Dang, Qun; Bai, Xu Synthetic Communications, 2010 , vol. 40, # 3 p. 361 - 369

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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 ( ...