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

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Authors	HAVEL Štěpán KHIRSARIYA PrashantKumar AKAVARAM Naresh PARUCH Kamil CARBAIN Benoit Jean-Pierre
Year of publication	2018
Type	Article in Periodical
Magazine / Source	The Journal of Organic Chemistry
MU Faculty or unit	Faculty of Science
Citation
Web	http://dx.doi.org/10.1021/acs.joc.8b02655
Doi	http://dx.doi.org/10.1021/acs.joc.8b02655
Keywords	synthesis; medicinal chemistry; building blocks; aminopyrazole; aminothiazole
Description	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.
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