Tandem radical cyclization of N-methacryloyl benzamides with CBr₄ to construct brominated isoquinolinediones

Abstract

Cumene promoted auto-oxidation involved tandem radical cyclization of N-methacryloyl benzamides using CBr4 as the bromine source to construct brominated isoquinolinediones is described.

A Visible Light and Iron‐mediated Carbocationic Route to Polysubstituted 1‐Halonaphthalenes by Benzannulation using Allylbenzenes and Polyhalomethanes

“…However, starting from 24 , product 3 b could be detected in small amounts. In addition, the bromo‐TEMPO adduct could be observed for both reactions via ESI‐MS [26] . These results confirm that the reaction proceeds via a radical pathway and also that ⋅Br and ⋅CBr 3 are not only involved in the Kharasch addition but also play a role in the subsequent benzannulation.…”

Copper-Catalyzed Phosphonylation/Trifluoromethylation of N-p-NO2-Benzoylacrylamides Coupled with Dearomatization and Denitration

“…When 3-MeO-4-NO 2 -benzoylacrylamide ( 1s ) was used as starting material, the desired dearomatization product 3s was obtained in 72% yield. The reaction of 3-NO 2 -benzoylacrylamide ( 1t ) under the standard conditions gave only the normal coupling product 3t in 41% yield; no dearomatization product was isolated . Both 2-NO 2 -benzoyl­acrylamide ( 1u ) and 2,4-di-NO 2 -benzoyl­acrylamide ( 1v ) under the standard conditions gave the same dearomatization product 3u in slightly lower yields.…”

Recent developments in the synthesis of the isoquinoline-1,3(2H,4H)-dione by radical cascade reaction

“…In 2018, Huang and co-workers described the synthesis of brominated isoquinoline-1,3(2 H ,4 H )-diones via the tandem cyclization of N -methacryloylbenzamides with CBr 4 . 67 The reaction provided a new method to generate bromine free radicals using a mild automatic oxidation pathway. The reaction showed a broad substrate scope.…”