Article Dans Une Revue Journal of Organic Chemistry Année : 2021

Base-Catalyzed Three-Component Reaction of α-Cyanoacetates with Chalcones and Elemental Sulfur: Access to 2-Aminothiophenes Unobtainable via the Gewald Reaction

Résumé

While Gewald reaction was well known for more than haft a century as an excellent method providing bioactive 2-aminothiophenes from reactions of α-cyanoacetates and carbonyl compounds and elemental sulfur, its application to dibenzoylmethanes as the carbonyl substrates was however unknown and experimentally proven unsuccessful. We proposed here a convenient approach to such series of compounds by a DABCO catalyzed, one-pot, two-step, three-component reaction of αcyanoacetate with chalcones and elemental sulfur. This catalytic strategy is highlighted by its excellent atom/step efficiency and high degree of structural diversification by simply choosing the suitable starting chalcones, which are unarguably much more readily available than dibenzoylmethanes.

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hal-03325821 , version 1 (25-08-2021)

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Thanh Binh Nguyen, Dinh Hung Mac, Pascal ́ Retailleau. Base-Catalyzed Three-Component Reaction of α-Cyanoacetates with Chalcones and Elemental Sulfur: Access to 2-Aminothiophenes Unobtainable via the Gewald Reaction. Journal of Organic Chemistry, 2021, 86 (14), pp.9418-9427. ⟨10.1021/acs.joc.1c00740⟩. ⟨hal-03325821⟩
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