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A comparative study on the synthesis of pyrazolo‐[4,3‐ c ]quinoline oxides by reductive cyclisations
Author(s) -
Sicker Dieter
Publication year - 1992
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.5570290152
Subject(s) - chemistry , quinoline , catalysis , oxide , catalytic hydrogenation , combinatorial chemistry , reductive elimination , medicinal chemistry , organic chemistry , stereochemistry
Alternate routes for the reductive cyclisation of 4‐acetyl‐3‐methyl‐5‐(2‐nitrophenyl)‐1‐phenylpyrazole under different conditions are described. Whereas 3,4‐dimethyl‐1‐phenylpyrazolo[4,3‐c]quinoline 5‐oxide is formed by mild noncatalytic reductions, catalytic and transfer hydrogenation processes cause the diastereoselective formation of cis ‐4,11‐dihydro‐3,5‐dimethyl‐1‐phenylpyrazolo[4,3‐ c ]quinoline 6‐oxide.