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Preparation and alkylation of regioisomeric tetrahydrophthalimide‐substituted indolin‐2(3 H )‐ones
Author(s) -
Karp Gary M.,
Condon Michael E.
Publication year - 1994
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.5570310639
Subject(s) - chemistry , alkylation , nitration , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis
A series of novel regioisomeric tetrahydrophthalimide‐substituted indolin‐2‐ones has been prepared via the Sommelet‐Hauser type cyclization of appropriately substituted anilines as potential herbicides. The resultant indolin‐2‐ones were then regioselectively alkylated at N‐1 and C‐3 to give 1,3,3‐trisubstituted indolin‐2‐ones. The most active series was also prepared by the bis ‐nitration of m ‐fluorophenylacetic acid followed by reduction and cyclization to give 6‐amino‐5‐fluoroindolin‐2‐one. Elaboration to the tetrahydrophthalimide‐substituted indolin‐2‐one was followed by C ‐ and N ‐alkylation to give the desired compounds.