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An efficient synthetic method for structurally various isochromenoindolones has been demonstrated through Rh(III)-catalyzed C-H activation followed by a cyclization reaction of N-methoxyarylamides with 3-diazooxindoles. The sequential reaction involves the streamlined formation of C-C and C-O bonds in one pot. The present method provides a broad range of isochromenoindolones as a new privileged scaffold in moderate to good yields with the release of methoxyamine and molecular nitrogen and has the benefits of a broad substrate scope and good functional group tolerance., (© 2021 Wiley-VCH GmbH.)