Citation: Wei Guo. Base mediated direct C-H amination for pyrimidines synthesis from amidines and cinnamaldehydes using oxygen as green oxidants[J]. Chinese Chemical Letters, ;2016, 27(01): 47-50. doi: 10.1016/j.cclet.2015.09.012 shu

Base mediated direct C-H amination for pyrimidines synthesis from amidines and cinnamaldehydes using oxygen as green oxidants

Wei Guo ^a,b,,

1.
a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China;
2.
b Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, China

Corresponding author: Wei Guo,
Received Date: 4 August 2015
Available Online: 26 August 2015
Fund Project: We are grateful to the China Postdoctoral Science Foundation Funded Project(No. 2014M562165) (No. 2014M562165)

A direct metal-free C-H amination reaction of cinnamaldehydes and amidines to realize the synthesis of polysubstituted pyrimidines was developed in the presence of base. This greener synthetic methodology provides a straightforward approach to the synthesis of a variety of pyrimidine derivatives under mild reaction condition using oxygen as sole oxidants.
- C-H amination,
- Pyrimidines,
- Amidines,
- Cinnamaldehydes,
- Oxygen
References
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  [2](a) S. Lee, D. Lim, E. Lee, et al., Discovery of carbohybrid-based 2-aminopyrimidine analogues as a new class of rapid-acting antimalarial agents using imagebased cytological profiling assay, J. Med. Chem. 57(2014) 7425-7434;(b) F. Arioli, S. Borrelli, F. Colombo, et al., N-[2-Methyl-5-(triazol-1-yl)phenyl]-pyrimidin-2-amine as a scaffold for the synthesis of inhibitors of Bcr-Abl, ChemMedChem 6(2011) 2009-2018.
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  [6] M. Lin, Q.Z. Chen, Y. Zhu, Copper(Ⅱ)-catalyzed synthesis of pyrimidines from propargylic alcohols and amidine:a propargylation-cyclization-oxidation tandem reaction, Synlett 8(2011) 1179-1183.
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  [7] A. Guirado, E. Alarcón, Y. Vicente, et al., A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones, Tetrahedron Lett. 54(2013) 5115-5117.
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9. [9]
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10. [10]
  [10](a) Y. Zhu, R.G. Cornwal, H. Du, et al., Catalytic diamination of olefins via N-N bond activation, Acc. Chem. Res. 47(2014) 3665-3678;(b) D. Chen, H.J. Mo, D.B. Chen, Direct C-H amination for indole synthesis from N-Ts-2-styrylaniline derivatives catalyzed by copper salt, Chin. Chem. Lett. 26(2015) 969-972;(c) Q. Cai, M.C. Liu, B.M. Mao, et al., Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I₂/CuO-promoted tandem strategy, Chin. Chem. Lett. 26(2015) 881-884.
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  [11] Z. Shi, C. Zhang, C. Tang, et al., Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant, Chem. Soc. Rev. 41(2012) 3381-3430.
12. [12]
  [12] W. Wu, H. Jiang, Palladium-catalyzed oxidation of unsaturated hydrocarbons using molecular oxygen, Acc. Chem. Res. 45(2012) 1736-1748.
13. [13]
  [13] R.J. Altenbach, R.M. Adair, B.M. Bettencourt, et al., Structure-activity studies on a series of a 2-aminopyridimidine-containing histamine H4 receptor ligands, J. Med. Chem. 51(2008) 6571-6580.
14. [14]
  [14] L. Li, Y.L. Zhao, Q. Wang, Base-promoted oxidative C-H functionalization of α-amino carbonyl compounds under mild metal-free conditions:using molecular oxygen as the oxidant, Org. Lett. 17(2015) 370-373.
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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

Base mediated direct C-H amination for pyrimidines synthesis from amidines and cinnamaldehydes using oxygen as green oxidants

References

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通讯作者: 陈斌, bchen63@163.com