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The synthesis of 4‐(3,3‐dimethyl‐3 H ‐pyrrolo[2,3‐ f ]quinolin‐2‐yl)pyrazoles and 4‐(3,3‐dimethyl‐3 H ‐pyrrolo[3,2‐ h ]quinolin‐2‐yl)pyrazoles
Author(s) -
Rashidi A.,
Afghan A.,
Baradarani Mehdi M.,
Joule John A.
Publication year - 2009
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.18
Subject(s) - chemistry , quinoline , hydrazine (antidepressant) , reagent , medicinal chemistry , stereochemistry , organic chemistry , chromatography
5‐Hydrazinoquinoline and 8‐hydrazinoquinoline were converted via Fischer syntheses with 3‐methyl‐butan‐2‐one into pyrido‐indolenines 2,3,3‐trimethyl‐3 H ‐pyrrolo[2,3‐ f ]quinoline 7 and 2,3,3‐trimethyl‐3 H ‐pyrrolo[3,2‐ h ]quinoline 11 , respectively. Exposure of the indolenines to the Vilsmeier reagent produced aminomethylene‐malondialdehydes 8 and 12 , which reacted with hydrazine or arylhydrazines to give 4‐(3 H ‐pyrrolo[2,3‐ f ]quinolin‐2‐yl)‐ and 4‐(3 H ‐pyrrolo[3,2‐ h ]quinolin‐2‐yl)‐pyrazoles, 9 and 13 . J. Heterocyclic Chem., 46, 428 (2009).