Cyano‐Schmittel Cyclization through Base‐Induced Propargyl‐Allenyl Isomerization: Highly Modular Synthesis of Pyridine‐Fused Aromatic Derivatives
Authors:
- 12 November 2015
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 21 (51) , 18699-18705
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.Keywords
Funding Information
- National Natural Science Foundation of China (21125210, 21372249, 21421091)
- Chinese Academy of Science
- Major State Basic Research Development Program (2011CB808700)
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