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Cleavage of the CN Bond in Carbodiimides via Release of High Ring Strain: A New Strategy for the Selective Synthesis of 2‐Aminoaryl Alkynyl Imines
Author(s) -
Zhou Yi,
Chi Yue,
Zhao Fei,
Zhang WenXiong,
Xi Zhenfeng
Publication year - 2014
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.201304701
Subject(s) - cycloisomerization , chemistry , ring (chemistry) , ring strain , cleavage (geology) , bond cleavage , stereochemistry , strain (injury) , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , materials science , medicine , fracture (geology) , composite material
A novel pattern of the cleavage and reorganization of CN bond in the multicomponent reaction (MCR) of terminal alkynes or haloalkynes, carbodiimides, and benzynes is achieved for the first time to construct efficiently 2‐aminoaryl alkynyl imines. The selective formation and ring‐opening of the azetine intermediate with the high ring strain is essential for this reaction. Further transformation of 2‐aminoaryl alkynyl imines via the Cu‐catalyzed cycloisomerization is explored to provide steroselectively the bi‐, tri‐, and tetracyclic fused pyrrolines.