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- Title
A Facile Synthesis of 1-Substituted 3-Alkoxy-1 H-isoindoles Based on the Reaction of 2-(Dialkoxymethyl)phenyllithiums with Nitriles, Followed by Acid-Catalyzed Cyclization.
- Authors
Kuroda, Minami; Kobayashi, Kazuhiro
- Abstract
A two-step synthesis of 1-substituted 3-alkoxy-1 H-isoindoles 4 has been developed. Thus, the reaction of 2-(dialkoxymethyl)phenyllithium compounds, which are easily generated in situ by Br/Li exchange between 1-bromo-2-(dialkoxymethyl)benzenes 1 and BuLi in THF at −78°, with nitriles afforded [2-(dialkoxymethyl)phenyl]methanimines 2, which were treated with a catalytic amount of TsOH⋅H2O in refluxing CHCl3 to give the desired products in reasonable yields. Similarly, 3-aryl-1-ethoxy-1-methyl-1 H-isoindoles 7 have been prepared starting from 1-bromo-2-(1,1-diethoxyethyl)benzenes 5.
- Subjects
ISOINDOLE; NITRILES; CHLOROFORM; PHTHALAZINE; SILICA
- Publication
Helvetica Chimica Acta, 2015, Vol 98, Issue 3, p279
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201400333