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Cyano‐Schmittel Cyclization through Base‐Induced Propargyl‐Allenyl Isomerization: Highly Modular Synthesis of Pyridine‐Fused Aromatic Derivatives
Author(s) -
You Xu,
Xie Xin,
Chen Haoyi,
Li Yuxue,
Liu Yuanhong
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503374
Subject(s) - isomerization , propargyl , pyridine , chemistry , modular design , base (topology) , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , computer science , mathematics , programming language , mathematical analysis
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.