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 | Zendy

Lokhande Pradeep D. | Zendy; Hasanzadeh Kamal | Zendy; Khaledi Hamid | Zendy; Mohd Ali Hapipah | Zendy

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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 ).

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