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Directed lithiation of unprotected quinolinecarboxylic acids

✍ Scribed by Anne-Sophie Rebstock; Florence Mongin; François Trécourt; Guy Quéguiner

Book ID
104232306
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
58 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The lithium salts of quinoline-2-carboxylic acid and 4-methoxyquinoline-2-carboxylic acid undergo deprotonation at C3 when treated with LTMP in THF at -25 and 0°C, respectively. The lithium salts of quinoline-3-and -4-carboxylic acids are more prone to nucleophilic addition; nevertheless, they are deprotonated at C4 and C3, respectively, when treated with LTMP in THF at -50°C.

📜 SIMILAR VOLUMES

Directed lithiation of unprotected pyrid
Directed lithiation of unprotected pyridinecarboxylic acids
✍ Florence Mongin; François Trécourt; Guy Quéguiner 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 229 KB

The lithium salts of 2-, 3-and 4-pyridinecarboxylic acids undergo deprotonation at the position adjacent to the carboxylate group when treated with LTMP in THF at 0 °C, -50 °C and -25 °C, respectively. The lithiation conditions could be extended to chloronieotinic acids, and even to an activated ben