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

Stepan Havel; Prashant Khirsariya; Naresh Akavaram; Kamil Paruch; Benoit Carbain

doi:10.1021/acs.joc.8b02655

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

J Org Chem. 2018 Dec 21;83(24):15380-15405. doi: 10.1021/acs.joc.8b02655. Epub 2018 Dec 6.

Authors

Stepan Havel^{1

2}, Prashant Khirsariya^{1

2}, Naresh Akavaram^{1

2}, Kamil Paruch^{1

2}, Benoit Carbain^{1

2}

Affiliations

¹ Department of Chemistry, CZ Openscreen , Masaryk University , Kamenice 5 , 625 00 Brno , Czech Republic.
² International Clinical Research Center , St. Anne's University Hospital Brno , Pekařská 53 , 656 91 Brno , Czech Republic.

PMID: 30458618
DOI: 10.1021/acs.joc.8b02655

Abstract

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 α-arylation of β-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.

Publication types

Research Support, Non-U.S. Gov't