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Regioselective synthesis of bioactive spiro heterocyclic compounds containing both indoline and quinolone moieties by aryl radical cyclization
Author(s) -
Majumdar K. C.,
Kundu N.
Publication year - 2009
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.101
Subject(s) - chemistry , sodium hydride , indoline , potassium carbonate , regioselectivity , aryl , methyl iodide , anhydrous , medicinal chemistry , yield (engineering) , alkyl , organic chemistry , acetone , catalysis , materials science , metallurgy
The tin hydride‐mediated aryl radical cyclization of a number of 4‐(2′‐bromo‐ N ‐methylanilino)methyl‐1‐alkylquinolin‐2(1 H )‐ones under mild neutral condition afforded 1‐alkyl‐3,4‐dihydroquinolin‐2(1 H )‐one‐4‐spiro‐3′‐(1‐methylindolines) in excellent yield. The starting materials, amines were derived from 4‐bromomethyl‐ N ‐methyl quinolin‐2(1 H )‐ones and 2‐bromo‐ N ‐methyl anilines by refluxing in acetone in the presence of anhydrous potassium carbonate and sodium iodide (Finkelstein condition). J. Heterocyclic Chem., 46, 492 (2009).