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Novel Mannich-type nucleophilic substitution reaction with tertiary aromatic amines

✍ Scribed by Hiroyasu Takahashi; Nobuyuki Kashiwa; Yuichi Hashimoto; Kazuo Nagasawa

Book ID
104250870
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
64 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel formaldehyde-mediated condensation reaction of N,N-dialkyl aromatic amines and resonance-stabilized carbon nucleophiles is described. A condensation reaction between N,N-dimethylaniline (4) and ethyl acetoacetate (8) in the presence of formaldehyde in acetic acid took place to give 2-(4-dimethylaminobenzyl)-3-oxo butyric acid ethyl ester (9) together with the dimerization product 7 in 73 and 21% yields, respectively. This condensation reaction was further applied to the synthesis of 4-substituted dialkylaniline derivatives.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Novel Mannich-Type
ChemInform Abstract: Novel Mannich-Type Nucleophilic Substitution Reaction with Tertiary Aromatic Amines.
✍ Hiroyasu Takahashi; Nobuyuki Kashiwa; Yuichi Hashimoto; Kazuo Nagasawa πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 36 KB πŸ‘ 1 views

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Novel Petasis boronic acid–Mannich react
Novel Petasis boronic acid–Mannich reactions with tertiary aromatic amines
✍ Dinabandhu Naskar; Amrita Roy; William L. Seibel; David E. Portlock πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 113 KB

Tertiary aromatic amines can serve as amine substrates for the Petasis boronic acid-Mannich reaction, providing a practical synthetic route for the C C bond formation of a-(4-N,N-dialkylamino-2-alkyloxyphenyl)carboxylic acids. The scope and limitations of this method have been examined.