Transition‐Metal‐Mediated Routes to 3,3‐Disubstituted Oxindoles through Anilide Cyclisation

Abstract

This review describes transition-metal-catalysed and -mediated processes for the preparation of oxindoles from anilides through C(3)-C(3a) bond formation. Traditional methods,

Oxindole as starting material in organic synthesis

“…Alkylation of the dianion of oxindole 75 with 3-(4-methoxyphenyl)propyl iodide following the previous procedure 43 gave 41% yield of the C-3 monoalkylation product 79 which was converted to compound 80 using K 3 Fe(CN) 6 in dilute KOH. Compound 80 then rearranged to afford the crystalline phenol 81 in 91% yield (Scheme 27).…”

“…It is used for the treatment of infection, cancer, gastric ulcers, arthritis and other inflammatory processes. [1][2][3][4][5] Oxindole derivatives 6 have demonstrated significant potential for use in a wide range of biological applications such as NMDA antagonist 7 and calcium channel blockers 8 as well as antiangiogenic, Compound 12, resulted from the condensation of oxindole 1 with aldehyde 11 under microwave heating, was subjected to N-methylation and hydrogenation reaction to afford compound 13 in 95% yield. The following Mo-catalyzed asymmetric allylic alkylation reactions (AAA reactions) proceeded well and the allylated product 14 was isolated in 96% yield and 95% ee.…”

Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible‐Light Photoredox Catalysis

“…Among these, 1,2-acylarylation of methacrylamides has emerged as a particularly interesting approach. [10] However, the use of stoichiometric amounts of external oxidants, high temperature, or high-energy UV light represent considerable disadvantages of the procedures.…”

Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy

“…该反应历程为: 碘苯 1 和零价钯 氧化加成得中间体 2, 然后碳碳双键加成环化得中间体 3, 再与氰基进行配体交换得到中间体 4, 最后还原消除 得产物 3-烷基-3-氰甲基吲哚酮(Scheme 1). 从上面反应可以看出, 该反应底物的苯环或者烯烃 上都必须引入可以与过渡金属发生氧化加成的卤素或 者类卤素 [6] .…”