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Mukaiyama reagents in the synthesis of (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)ylidene]acetonitriles and their further electronic rearrangements effected by the action of acids and alkylating agents

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Abstract

Reactions of N-alkyl-2-chloropyridinium salts with benzimidazolylacetonitriles result in (E)-2-(1Hbenzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)-ylidene]acetonitriles. The alkylation of the latter with ω-bromoacetophenones in boiling acetone may gives rise to the N-alkylated salts, which are stabilized in two configurations, Z and E. The heating of the salts in acetonitrile causes their transformation into 2-(1H-benzo[d]-imidazol-2(3H)-ylidene(cyano)methyl)-1-methylpyridinium bromide due to the dearoylmethylation. The structure of the latter was proved by the XRD analysis.

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Authors and Affiliations

  1. Shevchenko Lugansk National University, ul. Oboronnaya, 2, Lugansk, 91011, Ukraine

    T. A. Saraeva & G. E. Khoroshilov

  2. Institute of Single Crystals, National Academy of Sciences of Ukraine, Khar’kov, Ukraine

    R. I. Zubatyuk & O. V. Shishkin

  3. Karazin Khar’kov National University, Khar’kov, Ukraine

    O. V. Shishkin

Authors
  1. T. A. Saraeva
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  2. G. E. Khoroshilov
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  3. R. I. Zubatyuk
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  4. O. V. Shishkin
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Corresponding author

Correspondence to G. E. Khoroshilov.

Additional information

Original Russian Text © T.A. Saraeva, G.E. Khoroshilov, R.I. Zubatyuk, O.V. Shishkin, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 4, pp. 659–664.

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Saraeva, T.A., Khoroshilov, G.E., Zubatyuk, R.I. et al. Mukaiyama reagents in the synthesis of (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)ylidene]acetonitriles and their further electronic rearrangements effected by the action of acids and alkylating agents. Russ J Gen Chem 82, 744–748 (2012). https://doi.org/10.1134/S1070363212040238

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  • DOI: https://doi.org/10.1134/S1070363212040238

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