Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides

doi:10.6023/cjoc202211003

Abstract

As a star molecule, N-arylacrylamides can undergo tandem radical addition/cyclization to efficiently construct C(3)-disubstituted indolin-2-ones. Indolin-2-ones are a class of important heterocyclic compounds with a wide range of biological activities, and the synthesis of which has been a research hotspot in the field of organic chemistry and medicinal chemistry. Silver catalysts are low in toxicity, and have unique catalytic activities, which are widely used in organic synthesis. In this paper, starting from different radical precursors and bond types (C—C, C—N, C—P, C—S), the research progress of silver-mediated synthesis of C(3)-disubstituted indolin-2-ones via tandem radical addition/cyclization of N-arylacrylamides is reviewed, and the representative substrates and reaction mechanisms are also summarized and discussed.

Key words: silver-mediated reaction, N-arylacrylamides, tandem cyclization, C(3)-disubstituted indolin-2-ones

Cite this article

Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.

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Fig. & Tab. 19

Figure 1. Some examples of drugs with an indolin-2-one backbone

Figure 2. Physostigmine and pyrrolidone drugs

Scheme 1. Decarboxylative acylarylation of α-oxocarboxylic acids

Scheme 2. Decarboxylative acylarylation of oxamic acids

Scheme 3. Alkyl/arylation of 1,3-dicarbonyl compounds

Scheme 4. Alkyl/arylation of cyclopropanols

Scheme 5. Decarboxylative aminoalkylation of amino acids

Scheme 6. Difluoromethylation of difluoroacetamides

Scheme 7. Difluoromethylation of difluoroacetate compounds

Scheme 8. Difluoromethylation of potassium difluoroarylacetate

Scheme 9. Difluoromethylation of difluoroarylacetic acids

Scheme 10. Ag-promoted azido-carbocyclization of activated alkenes via C—H bond cleavage

Scheme 11. Silver-catalyzed azido reaction of N-arylacrylamides

Scheme 12. Silver-promoted nitration of N-arylacrylamides

Scheme 13. Silver-catalyzed nitration of N-arylacrylamides

Scheme 14. Silver-catalyzed phosphonylation of N-arylacryl- amides

Scheme 15. Silver-promoted phosphonylation/azidization of acrylsulfonamides

Scheme 16. Silver-promoted trifluoromethylthiolation of N- arylacrylamides

Scheme 17. Silver-promoted thiocyanation of N-arylacrylamides

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