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A new rearrangement of spiro[indane-1,3′-thiophene] and spiro[naphthalene-1,3′-thiophene] derivatives accompanied by opening of the cycloalkane ring

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Abstract

The new thioamides 2-oxoindane-1-carbothioamides and 2-oxo-1,2,3,4-tetrahydronaphthalene-1-carbothioamides underwent conjugated addition to (E)-β-nitrostyrenes followed by cyclization to give products containing 5-hydroxyimino-2-aryliminothiophene rings spiro-annulated to the 2-indanone or 2-tetralone system. On treatment with hydrochloric acid in boiling methanol the compounds underwent a new rearrangement, involving transformation of the 2-aryliminothiophene ring to a pyrrole and an opening of the alicyclic ring in the proximity of the carbonyl group, affording 2-(1,3-diaryl-2-oxo-5-thioxopyrrol-4-yl)benzeneacetic or 2-(1,3-diaryl-2-oxo-5-thioxopyrrol-4-yl)benzenepropanoic acid methyl esters. The structures of two selected pyrrole derivatives were determined by X-ray crystal analyses. The thioamides derived from 2-indanone showed unexpected reactivity towards primary alcohols and underwent conversion to 2-hydroxy-1H-indene-3-thiocarboxylic acid O-esters.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Jagiellonian University, Kraków, Poland

    Krystyna Bogdanowicz-Szwed, Artur Budzowski & Regina Gil

  2. Andrzej Frycz Modrzewski Krakow University, Kraków, Poland

    Krystyna Bogdanowicz-Szwed, Artur Budzowski & Regina Gil

  3. Regional Laboratory, Jagiellonian University, Kraków, Poland

    Paweł Serda

Authors
  1. Krystyna Bogdanowicz-Szwed
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  2. Artur Budzowski
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  3. Regina Gil
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  4. Paweł Serda
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Correspondence to Artur Budzowski.

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Bogdanowicz-Szwed, K., Budzowski, A., Gil, R. et al. A new rearrangement of spiro[indane-1,3′-thiophene] and spiro[naphthalene-1,3′-thiophene] derivatives accompanied by opening of the cycloalkane ring. Monatsh Chem 141, 63–74 (2010). https://doi.org/10.1007/s00706-009-0233-4

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  • DOI: https://doi.org/10.1007/s00706-009-0233-4

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