Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (NH)-Benzo[ cd]indol-2(1 H)-ones from Naphthylamides

Jun Ying; Lu-Yang Fu; Guoqiang Zhong; Xiao-Feng Wu

doi:10.1021/acs.orglett.9b02037

Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (NH)-Benzo[ cd]indol-2(1 H)-ones from Naphthylamides

Org Lett. 2019 Jul 19;21(14):5694-5698. doi: 10.1021/acs.orglett.9b02037. Epub 2019 Jun 27.

Authors

Jun Ying¹, Lu-Yang Fu¹, Guoqiang Zhong¹, Xiao-Feng Wu^{1

2}

Affiliations

¹ Department of Chemistry , Zhejiang Sci-Tech University , Xiasha Campus, Hangzhou 310018 , People's Republic of China.
² Leibniz-Institut für Katalyse e. V. an der Universität Rostock , Albert-Einstein-Straβe 29a , 18059 Rostock , Germany.

PMID: 31246481
DOI: 10.1021/acs.orglett.9b02037

Abstract

A cobalt-catalyzed C-H carbonylation of naphthylamides for the synthesis of benzo[cd]indol-2(1H)-one scaffolds has been developed. The reaction employs a traceless directing group and uses benzene-1,3,5-triyl triormate as the CO source, affording various free (NH)-benzo[cd]indol-2(1H)-ones in moderate to high yields (up to 88%). Using this protocol, the total synthesis of BET bromodomain inhibitors A and B was accomplished as well.

Publication types

Research Support, Non-U.S. Gov't