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Facile and Efficient Synthesis of 3‐Pyrimidinyl Oxindoles by Phase‐Transfer‐Catalyzed Regioselective Nucleophilic Aromatic Substitution
Author(s) -
Brüning Fabian,
Katayev Dmitry,
Togni Antonio
Publication year - 2018
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.201800587
Subject(s) - regioselectivity , chemistry , nucleophilic aromatic substitution , nucleophilic substitution , catalysis , nucleophile , yield (engineering) , combinatorial chemistry , substitution reaction , phase transfer catalyst , functional group , electrophilic aromatic substitution , medicinal chemistry , organic chemistry , materials science , metallurgy , polymer
Phase‐transfer‐catalyzed regioselective nucleophilic aromatic substitution of 2,4‐dichloropyrimidines with N ‐Boc‐protected 3‐substituted oxindoles is reported. The reaction allows the formation of unsymmetrical all‐ carbon quaternary centers in the benzylic position of heteroaromatic scaffolds and proceeds with high chemical yield and excellent functional‐group tolerance. Various activated heteroaryl chlorides including dichloropyridazine and activated chloropyridines can also be reacted under the reaction conditions.