Article Dans Une Revue Comptes Rendus. Chimie Année : 2017

Intramolecular inverse electron-demand [4+2] cycloadditions of ynamidyl-tethered pyrimidines: Comparative studies in trifluorotoluene and sulfolane

Résumé

Three representative 6,7-dihydro-5H-cyclopenta[b]pyridin-4-amines were synthesized using an intramolecular inverse electron demand heteroeDielseAlder/retroeDielseAlder sequence between pyrimidines (acting as azadienes) and ynamides (acting as dienophiles). Two solvents of this reaction, sulfolane and trifluorotoluene, were compared at 210 C and the former consistently led to higher yields. In addition, these studies confirmed the importance of the steric bulk of the C5-position of the pyrimidinyl cycloaddition precursor.

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hal-02105042 , version 1 (19-04-2019)

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Morgan Donnard, Guillaume Duret, Philippe Bisseret, Nicolas Blanchard. Intramolecular inverse electron-demand [4+2] cycloadditions of ynamidyl-tethered pyrimidines: Comparative studies in trifluorotoluene and sulfolane. Comptes Rendus. Chimie, 2017, 20 (6), pp.643-647. ⟨10.1016/j.crci.2017.01.007⟩. ⟨hal-02105042⟩
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