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Mono‐, and dibenzacridine imines. Synthesis of 1a,11b‐ dihydrobenz[ c ]azirino[α]acridine, 4b,5a‐dihydrodibenz[ c,h ]‐ azirino[α]acridine and 1a,13b‐dihydrodibenz[ c,j ]azirino[α]acridine
Author(s) -
Bazanov Nina,
Dayan Yael,
Blum Jochanan,
Harvey Ronald G.
Publication year - 1994
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.5570310425
Subject(s) - acridine , chemistry , sodium azide , imine , tributylphosphine , azide , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The syntheses of the K‐imine derivatives of benz[ c ]acridine, dibenz[ c,h ]acridine and dibenz[ a,h ]acridine are described. The parent hydrocarbons 1, 6 and 11 were oxidized with sodium hypochlorite under phase transfer conditions to the corresponding K‐oxides 4,9 and 14 , which in turn were reacted with sodium azide. The resulting azido alcohols were then cyclized with tributylphosphine to the title compounds 5,10 and 15.