A Green Approach for the Electroorganic Synthesis of New Dihydroxyphenyl-indolin-2-one Derivatives

Abstract

In an aqueous solution containing oxindole as a nucleophile, electrochemical oxidation of 2,3-dimethylhydroquinone and some catechols have been studied using cyclic voltammetry and controlled potential coulometry. The voltammetric data show that electrochemically generated para- and ortho-benzoquinones participate in Michael addition reactions with oxindole to form the corresponding dihydroxyphenyl-indolin-2-one derivatives. In this work, we have proposed a mechanism for the electrode process, and we report an efficient and one-pot green method for the synthesis of dihydroxyphenyl-indolin-2-one derivatives based on the Michael reaction of electrochemically generated ortho- and para-benzoquinones with oxindole in an undivided cell using an environmentally friendly reagentless method in ambient conditions.

Electrochemical strategies for C–H functionalization and C–N bond formation

“…[675][676][677][678][679][680][681] Considering their relatively low oxidation potentials, it is perhaps unsurprising that an assortment of nucleophiles are compatible with these processes without being subjected to oxidation. Here, amines, [682][683][684][685][686][687][688][689] azide, 690,691 enolates and other carbon nucleophiles, [692][693][694][695][696][697][698][699][700][701][702][703][704][705][706][707][708][709][710][711] nitrate, 712 sulfinates [713][714][715][716][717][718][719][720][721][722][723]…”

Electrochemically Induced Michael Addition Reaction: An Overview

“…In an aqueous solution, electrochemical oxidation of 2,3‐dimethylhydroquinone and catechol derivatives were performed through cyclic voltammetry and controlled potential coulometry. The voltammetric data indicated that electrochemically produced ortho ‐ and para ‐ benzoquinone derivatives participate in Michael reactions using oxindole to provide the desired dihydroxyphenyl‐indolin‐2‐ones 202 (Scheme ) …”

“…The voltammetric data indicated that electrochemically produced ortho-and para-benzoquinone derivatives participate in Michael reactions using oxindole to provide the desired dihydroxyphenyl-indolin-2-ones 202 (Scheme 63). [75] A significant technique was reported for synthesis of butyrolactone derivatives 204 through electrochemical oxidation of catechol derivatives 151a-c in the presence of 3acetyldihydro-2(3H)-furanone 103 as a nucleophile in H 2 O-EtOH solution (90 : 10 v/v). The results indicated that the electro-generated o-benzo-quinone applied in a Michael addition reaction with this nucleophile through EC mechanism route (Scheme 64).…”

New insights into the electrochemical behavior of acid orange 7: Convergent paired electrochemical synthesis of new aminonaphthol derivatives

“…The concept and significance of green sustainable chemistry (GSC), has been recognized throughout the world, and nowadays new processes cannot be developed without consideration of GSC. In recent years, much attention has been paid to electroorganic synthesis as a typical environmentally friendly process [15][16][17][18][19][20][21][22][23] . This method contains the simultaneous incidence of both oxidation (at the anode) and reduction (at the cathode).…”

“…mp: 164-165 °C; isolated yield 62%. 1 H NMR (400 MHz, DMSO-d 6 ): δ = 6.33 (s, ~1 H, NH, this peak disappeared upon addition of D 2 O), 7.38 (dd, 2 H, J = 3.2 and 9.6 Hz, aromatic), 7.62 (d, 2 H, J = 8.8 Hz, aromatic), 7.85 (d, 2 H, J = 8.8 Hz, aromatic), 8.06 (d, 1 H, J = 2.8 Hz, aromatic), 8.19 (m, 1 H, aromatic), 8.28 (m, 1 H, aromatic), 9.92 (s, ~1 H, OH, this peak disappeared upon addition of D 2 O); 13 C NMR (100 MHz, DMSO-d 6 ): δ = 118.2, 120.6, 122.6, 123.1, 123.7, 124.3, 124.9, 125.0, 126.2, 128.8, 129.9, 136.7, 138.2, 142.0; IR (KBr): 3362, 3286, 3068, 1630, 1309, 1284, 1174, 1144, 1085, 906, 824, 781, 752, 648, 580 cm −1 ; MS (EI, 70 eV): m/z (relative intensity %): 333 (M + , 24), 174 (12), 158 (100), 130 (58), 111 (21), 103 (18), 77(17), 75 (28), 50(18).…”