Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction |
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Authors: | Yohei Ikuma Hiroyuki Nakahira |
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Institution: | Drug Research Division, Dainippon Sumitomo Pharma Co., Ltd., Kasugade Naka 3-1-98, Konohana-ku, Osaka 554-0022, Japan |
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Abstract: | Representatives of the 3H-imidazo4,5-c]quinolin-4(5H)-ones have shown interesting biological activity. We have found 2-aminosubstituted 3H-imidazo4,5-c]quinolin-4(5H)-one as a potent dipeptidyl peptidase 4 inhibitor. However effective synthesis of this nucleus with various substituents at the 6-9-positions has not been reported. We report herein the development of a novel and efficient synthesis of 2-aminosubstituted 3H-imidazo4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction. Our optimization of the reaction conditions revealed that the most important factors for this reaction are use of silver carbonate as a base and high reaction temperature. |
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Keywords: | 2-Aminosubstituted-3H-imidazo[4 5-c]quinolin-4(5H)-ones Palladium-assisted internal biaryl coupling reaction Silver carbonate High reaction temperature |
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