Preparation and alkylation of regioisomeric tetrahydrophthalimide-substituted indolin-2(3H)-ones

Autor: Gary M. Karp, Michael Edward Condon
Rok vydání: 1994
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 31:1513-1520
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570310639
Popis: 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.
Databáze: OpenAIRE
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