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The synthesis of 4-(3,3-dimethyl-3H-pyrrolo[2,3-f]quinolin-2-yl)pyrazoles and 4-(3,3-dimethyl-3H-pyrrolo[3,2-h]quinolin-2-yl)pyrazoles

✍ Scribed by A. Rashidi; A. Afghan; Mehdi M. Baradarani; John A. Joule

Publisher: Journal of Heterocyclic Chemistry
Year: 2009
Tongue: English
Weight: 136 KB
Volume: 46
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.18

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✦ Synopsis

Abstract

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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).

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