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Efficient synthesis of bromocyclopenta[ b ] indoles via a bromination ‐ reduction sequence
Author(s) -
Lachance Nicolas,
Chan Wing Yan
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.5570400214
Subject(s) - chemistry , bromine , halogenation , pyridine , adduct , sequence (biology) , medicinal chemistry , stereochemistry , double bond , organic chemistry , combinatorial chemistry , biochemistry
Substituted cyclopenta[ b ]indoles are selectively brominated in good yields with excess pyridine ‐ Br 2 charge‐transfer complex (PyBr 2 ) in a one‐pot reaction to provide 5 and/or 7‐bromoindoles. The mechanism involves the formation of an adduct (addition of bromine on the central double bond) which is subsequently reduced in situ with Zn and AcOH. A variety of functional groups in the cyclopentyl and the benzenoid rings are tolerated.