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Facile synthesis of 4-alkoxycarbonylisoquinoline-1,3-diones and 5-alkoxycarbonyl-2-benzazepine-1,3-diones via a mild alkaline cyclization

✍ Scribed by Muriel Billamboz; Fabrice Bailly; Philippe Cotelle

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
126 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A series of 4‐methoxycarbonylisoquinoline‐1,3‐diones was obtained from homophthalic acid in four steps. The key step was the quantitative and rapid alkaline cyclization of 2‐methoxycarbonyl‐2‐(2‐methoxycarbonylphenyl) acetamides. Homologation easily afforded in the same conditions 5‐carboxy‐2‐benzazepine‐1,3‐dione. J. Heterocyclic Chem., 46, 392 (2009).

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Syntheses and Reactions of 2,2-Disubstit
Syntheses and Reactions of 2,2-Disubstituted Cyclopentane-1,3-diones, 6. Conversion of 2-Methylcyclopentane-1,3-dione into 5-Methylcycloheptane-1,4-dione via 3-(1-Methyl-2,5-dioxocyclopentyl)propanal
✍ Schick, Hans ;Roatsch, Birgit ;Schwarz, Hartmut ;Hauser, André ;Schwarz, Sigfrid 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 453 KB

## Abstract In contrast to earlier reported unsuccessful experiments the Michael addition of prop‐2‐enal to 2‐methylcyclopentane‐1,3‐dione (1) affords 3‐(1‐methyl‐2,5‐dioxocyclopentyl)propanal (3) in 90% yield, if the reaction is carried out in water without a basic catalyst. This aldehyde is conve