Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
- 12 July 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (15), 5664-5668
- https://doi.org/10.1021/acs.orglett.1c01762
Abstract
We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical skeletons. Importantly, the late-stage derivatization of Momelotinib highlights the potential utility of this methodology.Keywords
Funding Information
- National Natural Science Foundation of China (21572162)
- Natural Science Foundation of Zhejiang Province (LY20B020015, Q21B050002)
This publication has 45 references indexed in Scilit:
- Nickel‐Catalyzed Construction of 2,4‐Disubstituted Imidazoles via C–C Coupling and C−N Condensation Cascade ReactionsAdvanced Synthesis & Catalysis, 2019
- Structure and Reactivity of Highly Twisted N-AcylimidazolesOrganic Letters, 2019
- Synthesis of substituted oxazoles via Pd-catalyzed tandem oxidative cyclizationOrganic Chemistry Frontiers, 2017
- A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and AlkoxylationThe Journal of Organic Chemistry, 2017
- A convenient strategy to 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives through silver-mediated oxidative C O cross coupling/cyclizationTetrahedron Letters, 2015
- Suzuki-Miyaura Cross-Coupling Reactions of Unprotected HaloimidazolesThe Journal of Organic Chemistry, 2014
- Low Power Visible-to-UV UpconversionThe Journal of Physical Chemistry A, 2009
- Muscarine, imidazole, oxazole and thiazole alkaloidsNatural Product Reports, 2009
- New Method for the Synthesis of Diversely Functionalized Imidazoles from N-Acylated α-AminonitrilesOrganic Letters, 2004
- Chemistry of oxazolesChemical Reviews, 1975