Wei-Jun Kong1, Xingrong Chen1, Mingming Wang1, Hui-Xiong Dai1,2, Jin-Quan Yu1,3. 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Shanghai 200032, China. 2. Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Road Zu Chong Zhi, Zhangjiang Hi-Tech Park, Shanghai, 201203, China. 3. Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Abstract
Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.
Here we report an aerobic Pd(0) catalyzed C2-H functionalization of n class="Chemical">indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.
Authors: Matthew E Voss; Percy H Carter; Andrew J Tebben; Peggy A Scherle; Gregory D Brown; Lorin A Thompson; Meizhong Xu; Yvonne C Lo; Gengjie Yang; Rui-Qin Liu; Paul Strzemienski; J Gerry Everlof; James M Trzaskos; Carl P Decicco Journal: Bioorg Med Chem Lett Date: 2003-02-10 Impact factor: 2.823