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Synthesis and Characterization of Amidato Divalent Lanthanide Complexes and Their Use in Forming 2,4‐Quinazolidinones from CO 2 and 2‐Aminobenzonitriles
Author(s) -
Wang Qianyu,
Lu Chengrong,
Zhao Bei,
Yao Yingming
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600291
Subject(s) - lanthanide , chemistry , divalent , catalysis , medicinal chemistry , stereochemistry , organic chemistry , ion
Four amidato divalent lanthanide complexes, {L n Ln[N(TMS) 2 ]THF} 2 [ n = 1, Ln = Eu ( 1 ); n = 2, Ln = Eu ( 3 ), Yb ( 4 ); HL 1 = t BuC 6 H 4 CONHC 6 H 3 ( i Pr) 2 ; HL 2 = C 6 H 5 CONHC 6 H 3 ( i Pr) 2 ] and {L 3 Eu[N(TMS) 2 ]THF}{L 3 2 Eu(THF) 2 } ( 2 ) [HL 3 = ClC 6 H 4 CONHC 6 H 3 ( i Pr) 2 ], were synthesized and extensively characterized. This is the first time that the amidato lanthanide amides 1 – 4 were used to catalyze the reactions of CO 2 and 2‐aminobenzonitriles to form quinazoline‐2,4(1 H ,3 H )‐diones at atmospheric pressure. All the complexes efficiently catalyzed the transformation, with complex 3 showing the highest activity. This catalytic system gave good to excellent yields, and good functional group tolerance. Preliminary studies were conducted to investigate the reaction mechanism.