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Darstellung C-4-substituierter Pyridazine durch homolytische Alkylierung bzw. Acylierung

Syntheses and reactions of pyridazine derivatives. 4th comm.: C-4 substituted pyridazines by homolytic alkylation and acylation

Synthesen und Reaktionen von Pyridazinderivaten, 4. Mitt.

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

Abstract

4-Benzyl-pyridazine (2) is prepared by homolytic benzylation of pyridazine (1). Oxidation of2 with KMnO4 or SeO2 yields 4-benzoyl-pyridazine (3). On treatment with NaBH4,3 is reduced quantitatively to the corresponding carbinol4. Reaction of protonated1 with benzoyl radicals affords mainly 4,5-dibenzoyl-pyridazine (5). The structures are proved by1H-NMR-, IR- and mass spectra.

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Literatur

  1. Mitt.:G. Heinisch, E. Luszczak undM. Pailer, Mh. Chem.104, 1372 (1973).

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  2. F. Minisci, Synthesis1973, 1.

  3. A. Clerici, F. Minisci undO. Porta, Tetrahedron29, 2775 (1973).

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  4. R. Mizzoni undP. Spoerri, J. Amer. Chem. Soc.76, 2201 (1954).

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  5. G. Gardini undF. Minisci, J. Chem. Soc.1970, 929.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie der Universität Wien, Währinger Straße 10, A-1090, Wien, Österreich

    G. Heinisch, A. Jentzsch & M. Pailer

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  1. G. Heinisch
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  2. A. Jentzsch
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  3. M. Pailer
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Heinisch, G., Jentzsch, A. & Pailer, M. Darstellung C-4-substituierter Pyridazine durch homolytische Alkylierung bzw. Acylierung. Monatshefte für Chemie 105, 648–652 (1974). https://doi.org/10.1007/BF00912616

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  • DOI: https://doi.org/10.1007/BF00912616

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