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Cyanoacetylene and Its Derivatives: XXXII. Addition of Ammonia and Methylamine to 4-Hydroxy-4,4-diphenyl-2-butynenitrile

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Abstract

Nucleophilic addition of ammonia (25% aqueous solution) and methylamine to 4-hydroxy-4,4-diphenyl-2-butynenitrile occurs under mild conditions to afford 4-amino(or methylamino)-2,5-dihydro-5,5-diphenyl-2-iminofurans. 4-Hydroxy-4,4-diphenyl-2-butynenitrile in anhydrous liquid ammonia gives rise to 3-amino-4-hydroxy-4,4-diphenyl-2- butenenitrile which is quantitatively converted into the corresponding iminodihydrofuran or iminodihydrofuran hydrochloride in the presence of 10 wt % of KOH or gaseous hydrogen chloride. 4-Amino- and 4-methylamino-2-iminofurans react with 4-hydroxy-4-methyl-2-pentynenitrile to give 3-(4-amino- and 4-methylamino-5,5-diphenyl-2,5-dihydrofuran-2-ylideneamino)-4-hydroxy-4-methyl-2-pentenenitriles.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. G. Mal’kina, L. V. Sokolyanskaya, R. N. Kudyakova, L. M. Sinegovskaya, A. I. Albanov, O. A. Shemyakina & B. A. Trofimov

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  1. A. G. Mal’kina
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  2. L. V. Sokolyanskaya
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  3. R. N. Kudyakova
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  4. L. M. Sinegovskaya
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  5. A. I. Albanov
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  6. O. A. Shemyakina
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  7. B. A. Trofimov
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 64–69.

Original Russian Text Copyright © 2005 by Mal’kina, Sokolyanskaya, Kudyakova, Sinegovskaya, Albanov, Shemyakina, Trofimov.

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Mal’kina, A.G., Sokolyanskaya, L.V., Kudyakova, R.N. et al. Cyanoacetylene and Its Derivatives: XXXII. Addition of Ammonia and Methylamine to 4-Hydroxy-4,4-diphenyl-2-butynenitrile. Russ J Org Chem 41, 61–66 (2005). https://doi.org/10.1007/s11178-005-0121-2

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  • DOI: https://doi.org/10.1007/s11178-005-0121-2

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