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Synthesen von Heterocyclen, 149. Mitt.: Über Reaktionen mit cyclischen Oxalylverbindungen, 3. Mitt.

Synthesis of heterocyclic compounds, CIL: Reactions of cyclic oxalyl compounds III

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Zusammenfassung

Propiophenon-N, N-diphenylhydrazon reagiert mit Oxalylchlorid zum 1-Diphenylamino-4-methyl-5-phenyl-2,3-dihydropyrrol-2,3-dion (1), welches sich beim Erhitzen auf 130–140° zum 2,3-Dioxo-8,8a-diphenyl-1,2,3,3a,8,8a-hexahydro-3a-methyl-pyrrolo[2,3-b]indol (2) isomerisiert. Analog verhalten sich Butyrophenon-N, N-diphenylhydrazon und Propiophenon-N-methyl-N-phenyl-hydrazon.

Abstract

Propiophenone-N, N-diphenylhydrazone reacts with oxalyl chloride to give 1-diphenylamino-4-methyl-5-phenyl-2,3-dihydropyrrole-2,3-dione (1), which is isomerized at 130–140° yielding 2,3-dioxo-8, 8a-diphenyl-1, 2, 3, 3a, 8, 8a-hexahydro-3a-methyl-pyrrolo[2,3-b]indole (2). Butyrophenone-N, N-diphenylhydrazone and propiophenone-N-methyl-N-phenyl-hydrazone react in a similar way.

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Authors and Affiliations

  1. Institut für Organische Chemie der Universität Graz, Graz, Österreich

    G. Kollenz, E. Ziegler, M. Eder & E. Prewedourakis

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  1. G. Kollenz
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  2. E. Ziegler
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  3. M. Eder
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  4. E. Prewedourakis
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Additional information

Herrn Prof. Dr.O. Hromatka, Techn. Hochschule Wien, mit Freundschaftlichen Grüßen und besten Wünschen zum 65. Geburtstag gewidmet.

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Kollenz, G., Ziegler, E., Eder, M. et al. Synthesen von Heterocyclen, 149. Mitt.: Über Reaktionen mit cyclischen Oxalylverbindungen, 3. Mitt.. Monatshefte für Chemie 101, 1597–1605 (1970). https://doi.org/10.1007/BF01152071

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  • DOI: https://doi.org/10.1007/BF01152071

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