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Aromatization and Halogenation of 3,3a,4,5‐Tetrahydro‐3‐aryl‐2‐phenyl‐2 H ‐benzo[g]indazole Using I 2 /DMSO, CuCl 2 /DMSO, and N ‐Bromosuccinimide
Author(s) -
Lokhande Pradeep D.,
Hasanzadeh Kamal,
Khaledi Hamid,
Mohd Ali Hapipah
Publication year - 2012
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.1049
Subject(s) - halogenation , chemistry , aromatization , indazole , aryl , medicinal chemistry , n bromosuccinimide , stereochemistry , organic chemistry , catalysis , alkyl
The treatment of 3,3a,4,5‐tetrahydro‐3‐aryl‐2‐phenyl‐2 H ‐benzo[g]indazoles 4 with I 2 /DMSO led to the oxidation of the five‐member rings ( 5 ) as well as the iodination of N ‐phenyl moieties along with oxidation of the five‐member rings ( 6 ). However, the reactions of 4 with CuCl 2 /DMSO gave only compounds 5 . The reaction of N ‐bromosuccinimide (NBS) with compounds 4 resulted in fully aromatization along with bromination at C‐5 of the indazole rings ( 7 ). The indazole six‐member rings in compounds 5 and 6 also underwent aromatization along with bromination by using NBS ( 7 and 8 ).