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Unexpected Formation of Thiophene in the Pyrrole Synthesis from Methoxyallene and Methyl Isothiocyanate

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Abstract

The sequential reaction of lithiated methoxyallene, methyl isothiocyanate, and 2-(bromomethyl)-1,3-dioxolane in the presence of CuBr yields a 2,3-disubstituted thiophene instead of the expected pyrrole. The process is accomplished in one preparative stage and involves intramolecular cyclization of the in situ-generated lithium allenylimidothioate and N-alkylation of the resulting lithium thienylamide. Varying the reaction conditions does not affect its route: in all cases, the only product is N-(1,3-dioxolan-2-ylmethyl)-3-methoxy-N-methylthiophen-2-amine.

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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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Authors and Affiliations

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

    O. A. Tarasova, N. А. Nedolya, А. I. Albanov & B. A. Trofimov

Authors
  1. O. A. Tarasova
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  2. N. А. Nedolya
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  3. А. I. Albanov
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  4. B. A. Trofimov
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Correspondence to N. А. Nedolya.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 2, pp. 285–290 https://doi.org/10.31857/S0514749221020154.

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Tarasova, O.A., Nedolya, N.А., Albanov, А.I. et al. Unexpected Formation of Thiophene in the Pyrrole Synthesis from Methoxyallene and Methyl Isothiocyanate. Russ J Org Chem 57, 287–291 (2021). https://doi.org/10.1134/S1070428021020214

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  • DOI: https://doi.org/10.1134/S1070428021020214

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