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Ir(I)‐Catalyzed Synthesis of ( E )‐4‐Benzylidenylacridines and ( E )‐2‐Styrylquinoline‐3‐carboxamide through Sequential Suzuki–Miyaura Coupling, Dehydrogenative Friedländer Reaction, and sp 3 ‐C–H Activation
Author(s) -
Prameela Soda,
Nawaz Khan FazlurRahman
Publication year - 2020
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.202000834
Subject(s) - chemistry , phenylboronic acid , quinoline , annulation , catalysis , suzuki reaction , medicinal chemistry , boronic acid , protonation , tartaric acid , coupling reaction , organic chemistry , combinatorial chemistry , palladium , ion , citric acid
An efficient one‐pot strategy evolved in the synthesis of (E)‐4‐benzylidenylacridin‐1(2H)‐ones, ( 4 or 9 ) (E)‐2‐styryl quinoline‐3‐carboxamides ( 5 or 10 ) by sequential Suzuki–Miyaura coupling‐dehydrogenative Friedländer‐sp 3 C–H activation. The 2‐amino‐5‐chloro benzhydrol 1 , aromatic alcohol 2 or 6 ketones 3 or 3' , and phenylboronic acid 7 underwent a smooth reaction in a basic deep eutectic solvent consisting of K 2 CO 3 and ethylene glycol (DES‐1,1:1). DES‐1 could enable the Pd‐catalyzed Suzuki coupling reaction of 6 , as well as the rapid oxidation of primary, secondary, and Suzuki coupled primary alcohols ( 2 , 1 , and 8 ) in the presence of an iridium catalyst and 1,10‐phenanthroline. The acidic DES‐2 (dimethyl urea/tartaric acid, 7:3) assists the Friedländer annulation and subsequent sp 3 ‐C–H functionalization resulting in (E)‐4‐benzylidenylacridin‐1(2H)‐ones ( 4 or 9 ) and (E)‐2‐styryl quinoline‐3‐carboxamides ( 5 or 10 ).