Cyano-Schmittel Cyclization through Base-Induced Propargyl-Allenyl Isomerization: Highly Modular Synthesis of Pyridine-Fused Aromatic Derivatives.
Chemistry
; 21(51): 18699-705, 2015 Dec 14.
Article
em En
| MEDLINE
| ID: mdl-26558737
ABSTRACT
The cyano-Schmittel cyclization of in situ-generated cyano-allenes has been carried out. The DFT calculation results suggest that the diradical pathway plays a major role in this cyclization. The reactions can be conveniently performed in a one-pot manner through cascade Sonogashira coupling of terminal cyano-ynes with organic halides, followed by base-promoted propargyl-allenyl isomerization/cyclization, leading to an efficient access to pyridine-fused polycyclic architectures. In particular, a large variety of aryl or heteroaryl rings such as furans, thiophenes and pyridines can be incorporated into the follow-up cyano-Diels-Alder reactions, highlighting the great synthetic utility of this chemistry.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2015
Tipo de documento:
Article