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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∗
a   College 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
b   Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Changde 415000, P. R. of China
c   Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology, Changde 415000, P. R. of China
,
Min Li
a   College 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
a   College 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
a   College 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
a   College 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∗
a   College 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
› Author AffiliationsThe authors are grateful for financial support from Hunan Provincial Natural Science Foundation of China (2020JJ5390 and 2020JJ4445), Scientific Research Fund of Hunan Provincial Education Department (19C1254 and 19B390), and the Technology Innovation and Development Guidance Program of Chang De (2020ZD16).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1469-5742.
  • Supporting Information


Publication History

Received: 26 March 2021

Accepted after revision: 29 March 2021

Accepted Manuscript online:
29 March 2021

Article published online:
10 May 2021

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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.