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Synlett 1990; 1990(11): 707-708
DOI: 10.1055/s-1990-21220
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The Synthesis of Stable 8-Alkylidene-9H-pyrazolo[4,3-d]tetrazolo [1,5-b]pyridazine Azomethine Imines and Their Transformation into 9,10-Dihydro-8H-tetrazolo[1',5' :1,6]-pyridazino [4,5-c] [1,2] diazepines, Derivatives of a Novel Heterocyclic System

Marko Žličar* , Branko Huč, Branko Stanovnik, Miha Tišler
  • *Department of Chemistry, Edvard Kardelj University, YU-61000 Ljubljana, Yugoslavia
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Publikationsdatum:
08. März 2002 (online)

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The NH,NH-dihydro cycloadducts 4 (9,9-dialkyl-6-chloro-7,8-dihydro-9H-pyrazolo[4,3-d]tetrazolo [1,5-b]pyridazines), obtained by the cycloaddition of diazoalkanes 2 with 6-chlorotetrazolo[1,5-b]pyridazine (1) at low temperature, react with carbonyl compounds 5 such as acetone and hexadeuteroacetone to give the stable azomethine imines 6, which thermally rearrange to tetrazolo[1',5' :1,6]pyridazino[4,5-c][1,2]diazepines (7).