t-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines

Abstract

The 2-amino-1,4-naphthoquinones and 2-amino-3-indolylnaphthoquinones by the t-BuOK mediated oxidative coupling amination has been developed. The 2-amino-3-indolylnaphthoquinones were conducted further transformation to polycyclic N-heterocycles.

Metal‐Free, PhI(OAc)2‐Promoted Oxidative C(sp2)−H Difunctionalization: Synthesis of Thioaminated Naphthoquinones

“…After that 1,4-naphthoquinone was regenerated by the aerobic oxidation of hydroquinone. [57][58][59][60] In this context, we were able to separate an intermediate 7 which was mentioned in the control experiment section. On the other hand, recently it has been shown that in the presence of hypervalent iodine (III) PIDA, thiophenol can generate sulfenium ion.…”

Silver-Catalyzed One-Pot Biarylamination of Quinones with Arylamines: Access to N-Arylamine-Functionalized p-Iminoquinone Derivatives

“…43, 160.56, 160.14, 158.32, 156.535 (CF, 1 J C,F = 227.3 Hz), 147.51, 142.08, 135.52, 135.29, 134.07, 131.39, 130.55, 126.38, 125.19, 125.07, 124.99, 123.04 (CF, 3 J C,F = 8.1 Hz), 116.18 (CF, 2 J C,F = 22.6 Hz), 115.80. 19 32, 155.42, 149.90, 141.56, 138.36, 135.10, 134.17, 131.54, 130.54, 129.36, 129.18, 128.53, 128.05, 126.45, 125.28, 124.21, 123.18, 97.67. HRMS: m/z calcd for C 22 H 15 Cl 2 N 2 O + (M + H) + : 393.0561; found: 393.0564.…”

“…05, 181.65, 148.77, 135.25, 133.65, 132.54, 130.84, 126.30, 125.75, 99.61, 37.09, 13.42. 19 Red solid; yield: 54.8 mg (85%); mp 167-169 °C.…”

(NH4)2S2O8-Promoted Direct C–C Coupling of Indoles with Quinones/Hydroquinones without Catalyst

“…Moreover, when 3aa and aniline (5a) were used as the substrates, 2-amino-3-indolylnaphthoquinone 6a was obtained in 85% isolated yield using t-BuOK (2 equiv) in DMF (2 mL) at room temperature for 2 h (Scheme 4b). 15 When 3aa and aniline (5a) were used with CoCl 2 (3 mol%), t-BuOK (1.5 equiv), and DMF (2 mL) at 120 °C for 24 h, the polycyclic N-heterocycle 7a was obtained in 86% isolated yield (Scheme 4c). 16 Polycyclic N-heterocycles are the key structural elements of natural products, drugs, and functional materials.…”