Base-Catalyzed Three-Component Reaction of α-Cyanoacetates with Chalcones and Elemental Sulfur: Access to 2-Aminothiophenes Unobtainable via the Gewald Reaction.
J Org Chem
; 86(14): 9418-9427, 2021 07 16.
Article
en En
| MEDLINE
| ID: mdl-34197118
ABSTRACT
Although the Gewald reaction was well-known for more than half 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 propose here a convenient approach to such a series of compounds by a DABCO-catalyzed, one-pot, two-step, three-component reaction of α-cyanoacetate 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.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Chalconas
Idioma:
En
Revista:
J Org Chem
Año:
2021
Tipo del documento:
Article
País de afiliación:
Francia