Access to the Cinnoline Scaffold via Rhodium-Catalyzed Intermolecular Cyclization under Mild Conditions

作者：Song, Chao; Yang, Chen; Zhang, Feifei; Wang, Jinhu; Zhu, Jin^*

来源：Organic Letters, 2016, 18(18): 4510-4513.

DOI：10.1021/acs.orglett.6b02103

• C-H ACTIVATION
• N BOND FORMATION
• 3,4-DISUBSTITUTED CINNOLINES
• INTERNAL ALKYNES
• DIAZO-COMPOUNDS
• H/O-H
• FUNCTIONALIZATION
• INHIBITORS
• ISOQUINOLINES
• DERIVATIVES

Herein, we report Rh(III)-catalyzed, N-amino (hydrazine) directed C-H functionalization with alpha-diazo-beta-ketoesters for access to the cinnoline scaffold. A diverse set of nondiscriminating conditions obtained for a highly efficient test transformation prompted use of a substrate-replacement technique for an in-depth search of experimental parameter space and pinpointing of the optimized conditions. A successive C-H activation/C-C coupling/intramolecular dehydration mechanistic sequence is proposed. The ability to perform gram-scale synthesis proves the synthetic utility of this simple, yet efficient, method.

• 出版日期2016-9-16
• 单位南京大学