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3 H ‐indolium salts efficiently prepared from N ‐substituted anilines and α‐branched ketones by an one‐pot synthesis
Author(s) -
Zimmermann Thomas,
Brede Ortwin
Publication year - 2004
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.5570410117
Subject(s) - chemistry , sodium nitrite , hydrazone , nitrosation , organic chemistry , zinc , sequence (biology) , nitrite , medicinal chemistry , nitrate , biochemistry
Starting with the N ‐substituted anilines 4/12 and the α‐branched ketones 3 the 3 H ‐indolium salts 1 and their fused derivatives 13 are prepared by combining a sodium nitrite nitrosation, a zinc dust reduction, a hydrazone formation and a Fischer indolization to a reaction sequence in which the isolation and purification of intermediates is not necessary. The scope and limitations of this effective one‐pot synthesis are discussed.