Premium
Synthesis and ring closure reactions of pyrido[3,2,1‐ jk ]carbazol‐6‐ones
Author(s) -
Dang Hoai V.,
Knobloch Bernd,
Habib Nargues S.,
Kappe Thomas,
Stadlbauer Wolfgang
Publication year - 2005
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.5570420112
Subject(s) - chemistry , thermal decomposition , ring (chemistry) , alkyl , medicinal chemistry , derivative (finance) , indole test , azide , closure (psychology) , reaction conditions , organic chemistry , catalysis , financial economics , economics , market economy
4‐Hydroxy‐5‐phenylpyrido[3,2,1‐ jk ]carbazol‐6‐ones ( 4, 5 ), which were obtained from carbazoles 1 and malonates 2 or 3 , were converted to reactive intermediates such as 4‐chlorides 9 or 4‐tosylates 10 , which gave in turn 4‐azido‐5‐phenyl derivatives 11 . 5‐Alkyl‐4‐azides 11 were not obtained in this manner; however a new one‐pot azidation reaction was developed starting from 4‐hydroxy derivatives 4 which gave azides 11 in good yields. 4‐Azido‐5‐phenyl derivative 11f cyclized on thermolysis to the indole 12 . The thermal behaviour of the azides 11 was studied by thermoanalytical methods (DSC).