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An unexpected replacement of a methyl with an amino in the tetramethylpyrazine system

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Abstract

A novel and unexpected product, 5-amino-3,6-dimethyl-2-pyrazinecarbonitrile (3), was obtained during the attempted to synthesis of 3,5,6-trimethyl-2-pyrazinecarbonitrile (2) from its corresponding alcohol (1) by the catalytic amount of KI or I2 in combination with TBHP as an external oxidant. The product was confirmed by ESI–MS, HRMS, 1H-NMR, 13C-NMR, and 2D-NMR. The mechanism for the formation of the amino group in the tetramethylpyrazine system is also proposed.

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Fig. 1
Scheme 1
Scheme 2
Scheme 3

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Authors and Affiliations

  1. Institute of New Drug Research, Jinan University College of Pharmacy, Guangzhou, 510632, China

    Ming Lang, Hui Yao, Pengfei Fu, Wei Cai, Yuqiang Wang & Pei Yu

Authors
  1. Ming Lang
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  2. Hui Yao
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  3. Pengfei Fu
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  4. Wei Cai
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  5. Yuqiang Wang
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  6. Pei Yu
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Corresponding author

Correspondence to Pei Yu.

Additional information

Ming Lang, Hui Yao: These authors contributed equally to this work.

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Lang, M., Yao, H., Fu, P. et al. An unexpected replacement of a methyl with an amino in the tetramethylpyrazine system. Res Chem Intermed 41, 5621–5626 (2015). https://doi.org/10.1007/s11164-014-1686-6

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  • DOI: https://doi.org/10.1007/s11164-014-1686-6

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