Preparation of 3,4-Substituted-5-Aminopyrazoles and 4 Substituted-2-Aminothiazoles

• Autoři: HAVEL Štěpán; KHIRSARIYA PrashantKumar; AKAVARAM Naresh; PARUCH Kamil; CARBAIN Benoit Jean-Pierre
• Rok publikování: 2018
• Druh: Článek v odborném periodiku
• Časopis / Zdroj: The Journal of Organic Chemistry
• Fakulta / Pracoviště MU: Přírodovědecká fakulta
• www: http://dx.doi.org/10.1021/acs.joc.8b02655
• Doi: http://dx.doi.org/10.1021/acs.joc.8b02655
• Klíčová slova: synthesis; medicinal chemistry; building blocks; aminopyrazole; aminothiazole
• Popis: 3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated alfa-arylation of beta-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

Související projekty

• Novel efficient and selective inhibitors of MRE11 nuclease and their potential therapeutic implications
• CZ-­OPENSCREEN: National Infrastructure for Chemical Biology