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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Authors: | T A Saraeva G E Khoroshilov R I Zubatyuk O V Shishkin |
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Institution: | 1. Shevchenko Lugansk National University, ul. Oboronnaya, 2, Lugansk, 91011, Ukraine 2. Institute of Single Crystals, National Academy of Sciences of Ukraine, Khar’kov, Ukraine 3. Karazin Khar’kov National University, Khar’kov, Ukraine
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Abstract: | Reactions of N-alkyl-2-chloropyridinium salts with benzimidazolylacetonitriles result in (E)-2-(1Hbenzod]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-benzod]-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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