Citation: Qi Sun, Cheng-Jun Wang, Shan-Shan Gong, Yong-Jian Ai, Hong-Bin Sun. Cp₂ZrCl₂-catalyzed synthesis of 2-aminovinyl benzimidazoles under microwave conditions[J]. Chinese Chemical Letters, ;2015, 26(3): 297-300. doi: 10.1016/j.cclet.2014.11.014 shu

Cp₂ZrCl₂-catalyzed synthesis of 2-aminovinyl benzimidazoles under microwave conditions

1.
a Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China;
2.
b Department of Chemistry, Northeastern University, Shenyang 110819, China

Corresponding author: Qi Sun, Hong-Bin Sun,
Received Date: 15 August 2014
Available Online: 13 October 2014
Fund Project: and Research Funds (Nos. ky2012zy08 and 2013QNBJRC001) from JXSTNU for financial support. (No. 212092)

A microwave-assisted general method for the synthesis of 2-aminovinyl benzimidazoles has been developed. Treatment of the 1,2-phenylenediamines and N-arylated/N,N-dialkylated 3-aminoacroleins with bis(cyclopentadienyl)zirconium(IV) dichloride (Cp₂ZrCl₂) as the catalyst under microwave irradiation for 3-5 min followed by in situ MnO₂ oxidation afforded thirteen 2-aminovinyl benzimidazoles in good yields.
- Benzimidazoles,
- Cp₂ZrCl₂,
- 3-Aminoacroleins,
- Microwave
References
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  [12] (a) Z.H. Zhang, L. Yin, Y.M. Wang, An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids, Catal. Commun. 8 (2007) 1126-1131; (b) R.R. Nagawade, D.B. Shinde, Zirconyl(IV) chloride-promoted synthesis of benzimidazole derivatives, Russ. J. Org. Chem. 42 (2006) 453-454.
13. [13]
  [13] K. Deo, S. Kanwar, A. Pandey, et al., Process for the preparation of N-methyl anilino acrolein, WO 2005090256, Chem. Abstr. 145 (2006) 292712.
14. [14]
  [14] (a) G. Navarrete-Vázquez, H. Moreno-Diaz, F. Aguirre-Crespo, et al., Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1Hbenzimidazole derivatives as constrained stilbene bioisosteres, Bioorg. Med. Chem. Lett. 16 (2006) 4169-4173; (b) R.G. Jacob, L.G. Dutra, C.S. Radatz, et al., Synthesis of 1,2-disubstituted benzimidazoles using SiO2/ZnCl2, Tetrahedron Lett. 50 (2009) 1495-1497.
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Cp2ZrCl2-catalyzed synthesis of 2-aminovinyl benzimidazoles under microwave conditions

References

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通讯作者: 陈斌, bchen63@163.com

Cp₂ZrCl₂-catalyzed synthesis of 2-aminovinyl benzimidazoles under microwave conditions