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

Abstract

In recent years, isoquinoline-1,3(2H,4H)-dione compounds have attracted extensive attention of synthetic chemists, they are committed to finding simple, mild, green and efficient synthetic methods. In this review, we summarized a...

A three-component reaction of cyclobutanone oxime esters, sulfur dioxide and N-alkyl-N-methacryloyl benzamides

“…13-1.22 (m, 2H), 0.81-0.87 (m, 1H), 0.62-0.67 (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 175. 6,164.5,139.6,133.9,129.6,128.4,125.2,125.1,118.0,61.6,53.7,45.9,31.1,24.6,18.0,16.1,8.6,8.1;HRMS (ESI) Organic & Biomolecular Chemistry Paper…”

“…5 Recently, the construction of isoquinoline-1,3-(2H,4H)-diones through the reaction of methacryloyl benzamide with radicals has been developed, including a cascade radical addition and cyclization process. 6 Various C4-functionalized isoquinoline-1,3-(2H,4H)-diones have been obtained by this strategy. 7 On the other hand, the importance of sulfonyl compounds in pharmaceuticals has led scientists to pay more attention to the implantation of sulfonyl groups into potential bioactive moieties in the last few decades.…”

“…5 Recently, the construction of isoquinoline-1,3-(2 H ,4 H )-diones through the reaction of methacryloyl benzamide with radicals has been developed, including a cascade radical addition and cyclization process. 6 Various C4-functionalized isoquinoline-1,3-(2 H ,4 H )-diones have been obtained by this strategy. 7…”

Palladium catalyzed tandem cyclization of acryloylbenzamides and N-arylacrylamides with epoxides: access to functionalized isoquinolinediones and oxindoles

“…12 Among the reported methodologies, the radical addition/tandem cyclization protocol of acryloylbenzamides and N -arylacrylamides has proven to be an efficient and attractive method for synthesizing isoquinolinediones and oxindoles owing to its simplicity, effectiveness, and high-step and atom economy. 13 Recently, various radical precursors, including alkyl, 14 acyl, 15 fluoroalkyl, 16 nitrogen, 17 sulfur, 18 silicon, 19 and phosphorus 20 -containing radicals, have been used in the tandem strategy. As part of our ongoing research program on the ring-opening coupling reaction of epoxides, we hypothesized that this tandem cyclization reaction can be extended to epoxides to access hydroxyalkylated isoquinolinediones and oxindoles.…”

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

“…There is a profound increase in research reports published yearly on the synthetic accomplishments in constructing the complex structures of the isoquinoline skeleton in non-racemic and enantiopure forms. [27][28][29][30][31] The studies on isoquinoline scaffolds offer new opportunities in medicinal and bioorganic chemistry due to their therapeutic applications. [32][33][34][35] Novel synthetic methodologies are reported in constructing isoquinoline skeletons instead revolving around the traditional Pictet-Spengler, Bischler-Napieralski, Pomeranz-Fritsch, and Bobbitt reaction procedures.…”