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Mass Spectra of New Heterocycles: XXV. Electron Ionization Study of N-[5-Aminothiophen-2-yl]thioureas

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Abstract

The electron ionization mass spectra of previously unknown N-(5-aminothiophen-2-yl)thioureas obtained in one preparative step from propargylamines and isothiocyanates were studied for the first time, and the main fragmentation patterns of these compounds were revealed. All the thienylthioureas studied form a molecular ion (Irel 7–61%), whose common fragmentation pathway {except for N-[5-(diethylamino)thiophen-2-yl]-N,N'-diphenylthiourea} is the cleavage of the R1N–C(=S) bond to form an intense [M – R2NHCS]+ ion peak (Irel 35–85%). The main fragmentation pathway of the molecular ions of N-[5-(diethylamino)thiophen-2-yl]-N,N'-diphenylthiourea is associated with the opening of the thiophene ring by the C2–S and C4–C5 bonds. N-[5-(Pyrrolidin-1-yl)thiophen-2-yl]- and N-[5-(piperidin-1-yl)thiophen-2-yl]thioureas characteristically undergo intense specific rearrangements that reveal themselves in the occurrence of unexpected primary fragmentation pathways of the molecular ions, the main of which is the elimination of an N,N'-dimethylcarbodiimide molecule.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

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  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    L. V. Klyba, E. R. Sanzheeva, N. A. Nedolya & O. A. Tarasova

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  1. L. V. Klyba
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  2. E. R. Sanzheeva
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  3. N. A. Nedolya
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  4. O. A. Tarasova
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Correspondence to L. V. Klyba.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 5, pp. 596–602 https://doi.org/10.31857/S0514749223050051.

For communication XXIV, see [1].

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Klyba, L.V., Sanzheeva, E.R., Nedolya, N.A. et al. Mass Spectra of New Heterocycles: XXV. Electron Ionization Study of N-[5-Aminothiophen-2-yl]thioureas. Russ J Org Chem 59, 776–781 (2023). https://doi.org/10.1134/S1070428023050056

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