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

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.

Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids

“…1, 137.1, 131.2, 129.5, 128.7, 128.6, 126.7, 126.4, 124.4, 120.3, 106.5 Dibenzo [cd,f]indol-4(5H)-one (4fʹ). [20] 10 mg, 30% yield. Yellow solid after purification by column chromatography (eluent, ethyl acetate/petroleum ether, V∶V＝ 1∶10), m.p.…”

“…227～229 ℃ (lit. [20] 168.9, 135.6, 134.2, 129.3, 128.9, 127.7, 127.6, 126.9, 126.8, 126.6, 126.5, 125.2, 123.4, 123.3, 105.4 13 C NMR spectra for all products. The Supporting Information is available free of charge via the Internet at http://sioc-journal.cn/.…”

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

“…In this work, the authors used 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo-[b,d]thiophen-5-ium trifluoromethanesulfonate as a trifluoromethane source in combination with a robust nickel complex as catalyst (Scheme 70B). In the scope study, the authors not only described the successful synthesis of several activated compounds (225)(226)(227)(228), but they also used known biologically active substances as substrates for this methodology (Scheme 70C).…”

Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights

“…Very recently, a cobalt‐catalyzed carbonylation reaction of naphthylamides 12 was developed by the group of Wu to have access to non‐protected benzo[ cd ]indol‐2(1 H )‐ones 26 in moderate to very good yields (Scheme ) . Benzene‐1,3,5‐triyl triformate was used as a solid CO source and this protocol was applied to the synthesis of BET inhibitors.…”