Ring Closure Reactions of 4-Chloro-5-hydroxyalkylamino-6-nitro-3(2H)- pyridazinones: Synthesis of Novel Pyridazino-Fused Ring Systems

Olivér Éliás; Lázló Károlyházy; Géza Stájer; Veronika Harmath; Orsolya Barabás; Péter Mátyus

doi:10.3390/ecsoc-4-01820

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Ring Closure Reactions of 4-Chloro-5-hydroxyalkylamino-6-nitro-3(2H)- pyridazinones: Synthesis of Novel Pyridazino-Fused Ring Systems

Olivér Éliás

¹,

Lázló Károlyházy

¹,

Géza Stájer

²,

Veronika Harmath

³,

Orsolya Barabás

³,

Péter Mátyus

^{*

1}

¹ Institute of Organic Chemistry, Semmelweis University, 1092 Budapest, Hõgyes Endre utca 7, Hungary
² Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös utca 7, Hungary
³ Department of Theoretical Chemistry, Eötvös Lóránd University, 1117 Budapest, Pázmány Péter sétány 1, Hungary

Published: 11 September 2000 by MDPI in The 4th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-4-01820

Abstract: Cyclization of the title compounds may occur in various ways (e.g., with the participation of C-6 or C-4 atom of the pyridazinone ring) to form differently fused pyridazino ring systems. The regiochemistry was found to be particularly dependent on the length of the side chain: from the hydroxyethylamino derivatives pyridazino[3,4-b]oxazines, and from hydroxypropylamino derivatives pyridazino[3,4-b]oxazepine and pyridazino[4,5-b]oxazepine systems were formed.

Keywords: 4-chloro-5-hydroxyalkylamino-6-nitro-3(2H)-pyridazinone; pyridazino[3,4-b] oxazepines; pyridazino[4,5-b]oxazepines.

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