Regioselective symmetrical bromination of protected 2,2′‐biimidazole | Zendy

SanchezGarcia David | Zendy; Borros Salvador | Zendy; ll Santi | Zendy; Borrell Jose I. | Zendy; Colominas Carles | Zendy; Teixido Jordi | Zendy

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Regioselective symmetrical bromination of protected 2,2′‐biimidazole

Author(s) -

SanchezGarcia David,

Borros Salvador,

ll Santi,

Borrell Jose I.,

Colominas Carles,

Teixido Jordi

Publication year - 2002

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.5570390418

Subject(s) - chemistry , halogenation , regioselectivity , lithium (medication) , equivalent , medicinal chemistry , n bromosuccinimide , stereochemistry , organic chemistry , catalysis , medicine , biochemistry , endocrinology

Treatment of the benzyl and (trimethylsilylethoxymethyl) SEM protected 2,2′‐biimidazoles, 2a and 2b , with 2 equivalents of N ‐bromosuccinimide (NBS) allows obtaining the 5,5′‐dibromo and 4,4′‐dibromo substituted biimidazoles, 3a and 5b respectively. The use of 4 equivalents of NBS, followed by treatment of the corresponding tetrabromoderivatives 4a and 5b with butyl lithium (BuLi), yields the 4,4′‐dibromoderiva‐tives 5a (G=Bn) and 5b (G=SEM).

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