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Further studies on heterocyclic arene imines. Preparation of 1a,9b‐dihydroazirino[ f ][1,7]phenanthroline, 3b,4a‐dihydroazirino‐[2,3]phenaleno[1,9‐ g,h ]quinoline and 1a,13b‐dihydrodibenzo[1,2:6,7]phenazino[1,2‐ b ]azirine
Author(s) -
BazanovKatz Nina,
Zangi Ronen,
Blum Jochanan
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330625
Subject(s) - chemistry , quinoline , phenazine , tributylphosphine , sodium azide , phenanthroline , acetone , imine , aqueous solution , medicinal chemistry , azide , organic chemistry , catalysis
The syntheses of the K‐imine derivatives of 1,7‐phenanthroline, phenaleno[1,9‐ g,h ]quinoline, and dibenzo[ a,h ]phenazine are described. The parent heterocyclic compounds 4, 9 and 14 were oxidized to the corresponding K‐oxides, 5, 10 and 15 , which in turn were reacted with sodium azide in aqueous acetone. The resulting trans ‐azido alcohols were then cyclized with tributylphosphine to the title compounds 6, 11 and 16 .