FeCl3-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes.
Org Lett
; 25(22): 4086-4091, 2023 Jun 09.
Article
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| MEDLINE
| ID: mdl-37229529
ABSTRACT
FeCl3-catalyzed decyanation of α-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed to synthesize 2,4-diaryl quinolines. A broad range of aniline, aldehyde, and arylacetylene derivatives were well tolerated to access 2,4-diaryl quinolines in moderate to good yields. The control experiment studies suggested that the reaction proceeds through a nonradical pathway involving Povarov-type [4 + 2] annulation from the in situ generated iminium species. The synthetic application of this strategy (i) includes gram-scale synthesis and (ii) a continuous-flow process for a few representative compounds in a shorter reaction time (22 min) and (iii) worked well with styrene as a proof of concept.
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Quinolinas
/
Alquinos
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2023
Tipo del documento:
Article