Efficient Access to 2,6,8-Trisubstituted 4-Aminoquinazolines through Microwave-Assisted One-Pot Chemoselective Tris-Suzuki-Miyaura or SNAr/Bis-Suzuki-Miyaura Reactions in Water

摘要

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 SNAr/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.