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Synthesis of derivatives of 2-aminoimidazole and 2-iminoimidazolidine by cyclization of 1-aryl-2-(4,6-dimethylpyrimidin-2-yl)guanidines with α-bromocarbonyl compounds

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Chemistry of Heterocyclic Compounds Aims and scope

Cyclization of 1-aryl-2-(4,6-dimethylpyrimidin-2-yl)guanidines with α-bromoacetophenone and ethyl bromoacetate gave derivatives of 1,4-diphenyl-1H-imidazole-2-amine and 2-amino-1-phenylimidazolidin- 4-one respectively. The mechanism of the reaction was determined on the basis of quantum-chemical calculations, NOESY NMR spectroscopy, and X-ray crystallography.

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Authors and Affiliations

  1. Voronezh State University, Universitestskaya Pl., 1, Voronezh, 394006, Russia

    A. S. Shestakov, O. E. Sidorenko & Kh. S. Shikhaliev

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, 28 Vavilova Str., Moscow, 119991, Russia

    I. S. Bushmarinov & M. Yu. Antipin

Authors
  1. A. S. Shestakov
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  2. I. S. Bushmarinov
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  3. O. E. Sidorenko
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  4. Kh. S. Shikhaliev
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  5. M. Yu. Antipin
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Correspondence to A. S. Shestakov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, 107–116, January, 2011.

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Shestakov, A.S., Bushmarinov, I.S., Sidorenko, O.E. et al. Synthesis of derivatives of 2-aminoimidazole and 2-iminoimidazolidine by cyclization of 1-aryl-2-(4,6-dimethylpyrimidin-2-yl)guanidines with α-bromocarbonyl compounds. Chem Heterocycl Comp 47, 82–89 (2011). https://doi.org/10.1007/s10593-011-0723-2

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