Open AccessEfficient syntheses of 1,3-unsubstituted 1H-pyrazolo[3,4-b]quinolines
Author(s) -
Arash Afghan,
Mohammad Mehdi Baradarani,
J. A. Joule
Publication year - 2008
Publication title -
arkivoc
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.21
H-Index - 58
eISSN - 1551-7012
pISSN - 1551-7004
DOI - 10.3998/ark.5550190.0010.203
Subject(s) - chemistry , aldehyde , hydrazine (antidepressant) , ring (chemistry) , sequence (biology) , halogen , combinatorial chemistry , closure (psychology) , medicinal chemistry , organic chemistry , catalysis , chromatography , biochemistry , alkyl , economics , market economy
The synthesis of pyrazolo(3,4-b)quinolines from 2-chloro-3-formylquinolines is described. Direct reaction of the chloro-aldehydes with hydrazine was unsuccessful, but a very efficient sequence was developed in which protection of the aldehyde group was followed by displacement of the halogen by hydrazine, release of the aldehyde then leading to spontaneous ring closure giving the tricycles. The products were obtained in excellent yields.
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