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Synthesis of 10-Aryl-10H-naphtho[1,8a,8-fg]indazol-7-ones

✍ Scribed by Wolfgang Stadlbauer; Gerhard Hojas

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 40 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400502

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✦ Synopsis

Abstract

3‐Hydroxy‐2‐[1‐(arylhydrazono)ethyl]‐1__H__‐phenalen‐1‐ones 3, obtained from 2‐acetyl‐3‐hydroxy‐1__H__‐phenalen‐1‐one (1) and arylhydrazines 2, cyclize under acidic conditions to 8‐methyl‐10‐aryl‐10__H__‐naphtho‐[1,8a,8‐f__g]indazol‐7‐ones 4. Indazoles 4 are also obtained from 2‐acetyl‐3‐hydroxy‐1__H‐phenalen‐1‐one (1) and arylhydrazines 2 in a one‐pot reaction. 2‐Acetyl‐3‐azido‐1__H__‐phenalen‐1‐one (6) does not give 8‐methyl‐9‐arylamino‐9__H__‐naphtho[1,8a,8‐__f__g]indazol‐7‐ones via azide decomposition but gives again by nucleophilic replacement of the azide moiety in 6 the indazole 4.

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