Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones

Abstract

Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.

One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(iii)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor

“…On the other hand, 3a was not obtained in the absence of AgOAc or [RhCp*Cl 2 ] 2 (entries [13][14]. Further reactions using other nonpolar or polar solvents such as toluene, 2,2,2-tri-uoroethanol (TFE), acetonitrile, and ethanol provided 3a in lower yields (45-68%) (entries [15][16][17][18]. The structure of 3a was identied by the analysis of its spectral data.…”

“…15 In addition, Rh(III)-catalyzed annulation of benzamides with diazo compounds for isoquinolinones was reported (Scheme 1a). 16 Although a number of methods for the synthesis of isochromenones and quinolinones or isoquinolinones have been demonstrated, the direct construction of heterocycles bearing both isochromenones and quinolin-2ones are only reported sporadically. 17 Recently, the reported Pd(II)-catalyzed carbonylation of alkynes is one such example (Scheme 1b).…”

Copper‐Catalyzed Self‐Condensation of Benzamide: Domino Reactions towards Quinazolinones

“…[29,30,5] The most attractive feature of this methodology is that it is one-pot synthesis using inexpensive catalysts and single substrate. To the best of our knowledge, our research group is the first to report one-pot Ullmann-type synthesis of pharmacologically important quinazolinone scaffold from a single substrate (2-bromobenzamide).…”

C–H Functionalization of Aromatic Amides

“…In 2016, Lin and co‐workers developed the first example of an Rh‐catalyzed direct synthesis of isoquinolinones via C–H activation/annulation of aromatic amides and diazo compounds (Scheme ) . The reaction does not require the use of external oxidants, and no by‐products are produced except for the green and pollution‐free N 2 and H 2 O.…”