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Divergent One‐Pot Two‐Step Synthesis of Phosphoryl‐Substituted 4‐Quinolones and 3‐Indolinones
Author(s) -
Nuzhdin Ivan V.,
Murashkina Arina V.,
Bezzubov Stanislav I.,
Mitrofanov Alexander Yu.,
Beletskaya Irina P.
Publication year - 2025
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.202401423
Subject(s) - chemistry , catalysis , intramolecular force , combinatorial chemistry , reaction conditions , medicinal chemistry , stereochemistry , organic chemistry
Herein, an approach is developed for the selective two‐step synthesis of phosphoryl‐substituted 4‐quinolones and phosphoryl‐substituted 3‐indolinones. This is achieved through the reaction of (3‐(2‐iodoaryl)‐3‐oxoprop‐1‐yn‐1‐yl)phosphonates with anilines followed by Cu‐catalyzed intramolecular cyclization of the intermediately formed regioisomeric enamines, which are selectively formed under neat conditions or in the presence of a gold complex as a catalyst. This method allows for the synthesis of a series of phosphoryl‐substituted 4‐quinolones and phosphoryl‐substituted 3‐indolinones in good yields.