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Synthesis of Indolines via a SmI 2 Promoted Domino Nitro Reduction–Intramolecular aza ‐Michael Reaction
Author(s) -
Ferreira Ramos Josierika A.,
Araújo Carolina S.,
Nagem Tanus J.,
Taylor Jason G.
Publication year - 2015
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.1982
Subject(s) - chemistry , michael reaction , nitro , intramolecular force , indoline , domino , cascade reaction , medicinal chemistry , acetaldehyde , selective reduction , nitro compound , organic chemistry , combinatorial chemistry , catalysis , ethanol , alkyl
A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza ‐Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2‐(2‐nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This “one pot” strategy also permitted the expeditious synthesis of a 1,2,3,4‐tetrahydroquinoline, whereas the seven‐membered 2,3,4,5‐tetrahydrobenzoazepines compounds were not formed under these reaction conditions.