We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
A Convenient Synthesis of 1-Alkoxy-2-alkyl-1,2-dihydroisoquinoline-3,4-diones Utilizing the Reaction of 2-(Dialkoxymethyl)phenyllithiums with Dimethyl Oxalate.
- Authors
Kobayashi, Kazuhiro; Honda, Yuuya; Kuroda, Minami
- Abstract
A new and convenient method for the preparation of 1,2-dihydroisoquinoline-3,4-diones with alkoxy and alkyl groups at the 4- and 3-positions, respectively, using an easily operated three-step sequence starting from 2-(dialkoxymethyl)phenyl bromides has been developed. Thus, the starting materials are treated with BuLi to generate 2-(dialkoxymethyl)phenyllithiums, which are allowed to react with (COOMe)2 to give methyl 2-(dialkoxymethyl)phenyl-2-oxoacetates. These are then transformed into the corresponding secondary amides by the reaction with primary amines. Treatment of these keto amides with a catalytic amount of TsOH⋅H2O affords the desired products. In order to demonstrate the synthetic utility of these products, transformation of one of them into the corresponding isoquinoline-1,3,4(2 H)-trione derivative by the oxidation with PCC was achieved.
- Subjects
OXALATES; AMINES; BROMINE compounds; DEAMINATION; QUINOLINE
- Publication
Helvetica Chimica Acta, 2016, Vol 99, Issue 2, p125
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201500254