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Synthesis of 4-isobutyl substituted thiophenes byGewald reaction

Synthese von 4-isobutylsubstituierten Thiophenen durchGewald-Reaktion

  • Organische Chemie Und Biochemie
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Summary

TheGewald reaction of 4-methyl-2-pentanone with alkyl cyanoacetates was investigated. Alkyl 2-amino-4-isobutylthiophene-3-carboxylates (4) were formed, together withbis-(2-amino-3-alkoxycarbonyl-4-isobutyl-5-thienyl)-disulfides (5) and alkyl 2-amino-4-isobutyl-5-morpholinothiophene-3-carboxylates (6). The absence of any 4-methyl substituted aminothiophene in the product mixtures came up highly unexpected. The mechanism of the reaction is discussed with respect to previously reported suggestions.

Zusammenfassung

DieGewald-Reaktion von 4-Methyl-2-pentanon mit Cyanessigsäurealkylestern wurde untersucht. Dabei entstehen die 2-Amino-4-isobutylthiophen-3-carbonsäurealkylester4 als Hauptprodukte sowie diebis-(2-Amino-3-alkoxycarbonyl-4-isobutyl-5-thienyl)-disulfide5 und die 2-Amino-4-isobutyl-5-morpholinothiophen-3-carbonsäurealkylester6. 4-Methylsubstituierte Aminothiophene wurden überraschenderweise in den Produktgemischen nicht aufgefunden. Der Reaktionsmechanismus wird im Zusammenhang mit bereits publizierten Vorstellungen diskutiert.

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References

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Authors and Affiliations

  1. Institut für Pharmazie der Universität Leipzig, D-04103, Leipzig, Germany

    M. Gütschow, H. Schröter, G. Kuhnle & K. Eger

Authors
  1. M. Gütschow
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  2. H. Schröter
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  3. G. Kuhnle
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  4. K. Eger
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Additional information

Dedicated to Professor Dr.Karl Gewald on the occasion of his 65th birthday

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Gütschow, M., Schröter, H., Kuhnle, G. et al. Synthesis of 4-isobutyl substituted thiophenes byGewald reaction. Monatsh Chem 127, 297–303 (1996). https://doi.org/10.1007/BF00813795

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  • DOI: https://doi.org/10.1007/BF00813795

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