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Transformations of N-heteroarylformamidines and N-heteroarylformamidine oximes new syntheses and transformations of oxazolo[4,5—d]pyridazines

Transformationen von N-Heteroarylformamidinen und N-Heteroarylformamidinoximen. Neue Synthesen und Transformationen von Oxazolo[4,5—d]pyridazinen

  • Organische Chemie Und Biochemie
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Abstract

New syntheses of oxazolo[4,5—d]pyridazine derivatives7 and11 were achieved by the cyclization of substituted N-pyridazin-5-ylformamide oximes6 and10. Under mild reaction conditions the transformations of the substituted amino group at position 2 of the oxazolo[4,5—d]pyridazine system7 occured to produce the compounds11, 14, and15, while under more drastic reaction conditions the nucleophilic attack at carbon at position 2 followed by the ring opening of the oxazole part of the molecule was observed to give the compounds13, 16, 17 and18.

Zusammenfassung

Mittels Cyclisierung substituierter N-Pyridazin-5-ylformamidoxime6 und10 wurden neue Synthesemöglichkeiten von Oxazolo[4,5—d]pyridazinderivaten erschlossen. Bei milden Reaktionsbedingungen trat Transformation der substituierten Aminogruppe an Position 2 des Oxazolo[4,5—d]pyridazin-Systems unter Bildung der Verbindungen11, 14 und15 ein, währenddessen unter drastischeren Reaktionsbedingungen ein nucleophiler Angriff am Kohlenstoff-2, gefolgt von einer Ringöffnung unter Bildung der Verbindungen13, 16, 17 und18 eintrat.

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Authors and Affiliations

  1. Department of Chemistry, Edvard Kardelj University, YU-61000, Ljubljana, Yugoslavia

    Mario Merslavič, Branko Stanovnik & Miha Tišler

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  1. Mario Merslavič
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  2. Branko Stanovnik
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  3. Miha Tišler
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Merslavič, M., Stanovnik, B. & Tišler, M. Transformations of N-heteroarylformamidines and N-heteroarylformamidine oximes new syntheses and transformations of oxazolo[4,5—d]pyridazines. Monatsh Chem 116, 1447–1458 (1985). https://doi.org/10.1007/BF00810484

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  • DOI: https://doi.org/10.1007/BF00810484

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