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Reaktionen mit cyclischen Oxalylverbindungen, 26. Mitt. Cyclokondensation von 4,5-substituierten Thiophen- bzw. N-Alkylpyrrol-2,3-dionen mito-Phenylendiamin

Reactions of cyclic oxalyl compounds, 26. Cyclocondensation reaction of 4,5-substituted thiophene- and N-alkylpyrrol-2,3-diones witho-phenylendiamine

  • Organische Chemie Und Biochemie
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Abstract

4-Benzoyl-5-phenylthiophene-2,3-dione (1) reacts witho-phenylendiamine to give the quinoxaline derivative2 which cyclizes either to the furo[2,3-b]quinoxaline4 or to the thieno[2,3-b]quinoxaline5 depending on the reaction conditions. On the other hand, the pyrrol-2,3-diones6 ando-phenylendiamine combine yielding the pyrrolidino[2,3-b][1,5]benzodiazepine derivatives7. The structures of all compounds were confirmed by IR and13C NMR spectroscopic measurements based on X-ray structure determinations of4/5 (mixed crystal) as well as7 b.4/5 crystallize triclinically in the space group P1 (Nr. 2) with two molecules per cell, while7 b crystallizes monoclinically in space group P21/a (Nr. 14) with four molecules7 b and four moleculesDMSO per cell. The reaction pathways leading to the compounds2,4,5, and7 are briefly discussed.

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Graz, A-8010, Graz, Österreich

    Ewald Terpetschnig, Walter Ott & Gert Kollenz

  2. Max-Planck-Institut für Festkörperforschung, D-7000, Stuttgart 80, Bundesrepublik Deutschland

    Karl Peters, Eva-Maria Peters & Hans Georg von Schnering

Authors
  1. Ewald Terpetschnig
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  2. Walter Ott
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  3. Gert Kollenz
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  4. Karl Peters
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  5. Eva-Maria Peters
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  6. Hans Georg von Schnering
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Herrn em. Univ.-Prof. Dr.E. Ziegler zur Vollendung des 75. Lebensjahres mit besten Wünschen gewidmet.

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Terpetschnig, E., Ott, W., Kollenz, G. et al. Reaktionen mit cyclischen Oxalylverbindungen, 26. Mitt. Cyclokondensation von 4,5-substituierten Thiophen- bzw. N-Alkylpyrrol-2,3-dionen mito-Phenylendiamin. Monatsh Chem 119, 367–378 (1988). https://doi.org/10.1007/BF00810263

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  • DOI: https://doi.org/10.1007/BF00810263

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