Iron-Catalyzed Oxidative Radical Alkoxycarbonylation of Activated Alkenes with Carbazates toward Alkoxycarbonylated Benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Yucai Tang; Min Li; Hongxin Huang; Feifei Wang; Xia Hu; Xiangyang Zhang

doi:10.1055/a-1469-5742

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(12): 1219-1222
DOI: 10.1055/a-1469-5742

letter

Iron-Catalyzed Oxidative Radical Alkoxycarbonylation of Activated Alkenes with Carbazates toward Alkoxycarbonylated Benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Yucai Tang∗

^aCollege of Chemistry and Materials Engineering, Hunan Province Cooperative Innovation Center for the Construction and Development of Dongting Lake Ecological Economic Zone, Hunan University of Arts and Science, Changde 415000, P. R. of China

^bHunan Provincial Key Laboratory of Water Treatment Functional Materials, Changde 415000, P. R. of China

^cHunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology, Changde 415000, P. R. of China

,

Min Li

^aCollege of Chemistry and Materials Engineering, Hunan Province Cooperative Innovation Center for the Construction and Development of Dongting Lake Ecological Economic Zone, Hunan University of Arts and Science, Changde 415000, P. R. of China

,

Hongxin Huang

^aCollege of Chemistry and Materials Engineering, Hunan Province Cooperative Innovation Center for the Construction and Development of Dongting Lake Ecological Economic Zone, Hunan University of Arts and Science, Changde 415000, P. R. of China

,

Feifei Wang

^aCollege of Chemistry and Materials Engineering, Hunan Province Cooperative Innovation Center for the Construction and Development of Dongting Lake Ecological Economic Zone, Hunan University of Arts and Science, Changde 415000, P. R. of China

,

Xia Hu

^aCollege of Chemistry and Materials Engineering, Hunan Province Cooperative Innovation Center for the Construction and Development of Dongting Lake Ecological Economic Zone, Hunan University of Arts and Science, Changde 415000, P. R. of China

,

Xiangyang Zhang∗

^aCollege of Chemistry and Materials Engineering, Hunan Province Cooperative Innovation Center for the Construction and Development of Dongting Lake Ecological Economic Zone, Hunan University of Arts and Science, Changde 415000, P. R. of China

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Abstract

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Abstract

A FeCl₂·4H₂O-catalyzed oxidative alkoxycarbonylation of activated alkenes with carbazates toward alkoxycarbonylated benzimidazo[2,1-a]isoquinolin-6(5H)-ones has been established. The reaction proceeded smoothly to furnish a series of structurally diverse benzimidazo[2,1-a]isoquinolin-6(5H)-one frameworks in moderate to good yield.

Key words

iron catalysis - carbazates - hydrazinecarboxylates - alkoxycarbonylation - benzimidazoisoquinolinones - alkenes

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Referenzen

References and Notes

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13 Methyl (5-Methyl-6-oxo-5,6-dihydrobenzimidazo[2,1-a]isoquinolin-5-yl)acetate (3a): Typical Procedure 70% aq TBHP (1.0 mmol) was added to a mixture of 1-methacryloyl-2-phenyl-1H-benzimidazole (1; 0.25 mmol), methyl carbazate (1.25 mmol), and FeCl₂·4 H₂O (0.05 mmol) in MeNO₂ (2 mL), and the mixture was heated at 80 °C for 6 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography [silica gel, PE–EtOAc (4:1 to 6:1)] to give a white solid; yield: 40 mg (50%); mp 207–208 °C.¹H NMR (400 MHz, CDCl₃): δ = 8.51 (dd, J = 7.7, 1.6 Hz, 1 H), 8.39–8.34 (m, 1 H), 7.87–7.81 (m, 1 H), 7.57–7.35 (m, 5 H), 3.71 (d, J = 17.2 Hz, 1 H), 3.37 (s, 3 H), 3.21 (d, J = 17.2 Hz, 1 H), 1.64 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 172.8, 170.5, 149.8, 144.0, 141.7, 131.8, 131.5, 127.9, 126.3, 125.8, 125.5, 125.0, 122.9, 119.8, 116.6, 51.9, 46.5, 44.1, 30.1. HRMS (ESI): m/z [M + H]⁺ calcd for C₁₉H₁₇N₂O₃: 321.1239; found: 321.1235.

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