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In this study, we examine the site-selctive iridium(III)-catalyzed C–H amidation between 2-aryl azlactones and acyl azides. This transformation produces a range of ortho-amidated azlactones, which act as precursors for the synthesis of chiral amino acids via organocatalyzed ring-opening reactions. To test its effectiveness, the method developed is applied to the late-stage C–H amidation of complex drug molecules. The isolation of an iridacycle species supports a proposed reaction pathway. [ABSTRACT FROM AUTHOR]

The site‐selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)‐catalyzed C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with a range of nitrene surrogates including dioxazolones, organic azides, and N‐methoxyamides. Complete site‐selectivity and functional group tolerance are observed. Notably, the large‐scale reaction and late‐stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. [ABSTRACT FROM AUTHOR]

Cover Feature: Site-Selective C-H Amidation of 2-Aryl Quinazolinones Using Nitrene Surrogates (Eur. J. Org. B The Cover Feature b shows the rhodium(III) and iridium(III)-catalyzed C-H amidation reaction of 2-aryl quinazolin-4(3 I H i )-ones with a range of nitrene surrogates including dioxazolones dioxazolones, organic azides, and I N i -methoxyamides through I N i -assisted C-H activation. More information can be found in the Full Paper by S. Hong, I. S. Kim et al. GLO:5AG/13dec20:ejoc202001294-toc-0001.jpg PHOTO (COLOR): . gl B The Cover Feature b shows the rhodium(III) and iridium(III)-catalyzed C-H amidation reaction of 2-aryl quinazolin-4(3 I H i )-ones with a range of nitrene surrogates including dioxazolones dioxazolones, organic azides, and I N i -methoxyamides through I N i -assisted C-H activation. [Extracted from the article]