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Efficient Access to 2,6,8‐Trisubstituted 4‐Aminoquinazolines through Microwave‐Assisted One‐Pot Chemoselective Tris‐Suzuki–Miyaura or S N Ar/Bis‐Suzuki–Miyaura Reactions in Water
Author(s) -
Kabri Youssef,
Crozet Maxime D.,
Terme Thierry,
Vanelle Patrice
Publication year - 2015
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.201500162
Subject(s) - chemistry , suzuki reaction , amination , microwave irradiation , combinatorial chemistry , solvent , tris , aqueous medium , organic chemistry , aqueous solution , palladium , catalysis , biochemistry
An efficient, sequential, one‐pot strategy for synthesizing polyfunctionalized quinazoline derivatives is presented. After selective amination of 6,8‐dibromo‐2,4‐dichloroquinazoline at the C‐4 position, 2,6,8‐trisubstituted 4‐aminoquinazoline derivatives were prepared through one‐pot chemoselective sequential tris‐Suzuki–Miyaura or S N Ar/bis‐Suzuki–Miyaura reactions under microwave irradiation in an aqueous medium. This approach, used with a variety of boronic acids, affords polysubstituted quinazoline derivatives in good to excellent yields in only a few steps and in the environmentally benign solvent water.