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Synthesis of 10‐Aryl‐10H‐naphtho[1,8a,8‐ f g]indazol‐7‐ones
Author(s) -
Stadlbauer Wolfgang,
Hojas Gerhard
Publication year - 2003
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.5570400502
Subject(s) - chemistry , indazole , moiety , azide , nucleophile , decomposition , aryl , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
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 .