Trimethylsilyl enol ethers ( 1 ) reacted with l-ethoxycarbonylpyridinium chloride (2 ) at 4-position with high rezoselectivity to afford l-ethoxycarbonyl-4-( 2-oxoalkyl )-1,4\_dihydropyridines ( 2 ) in 42 -8'7% yields. When 2, 2, 2-trichloroethyl chloroformate was employed, yields of the correspond
Regioselective addition of titanium enolates to 1-acylpyridinium salts. A convenient synthesis of 4-(2-oxoalkyl)pyridines
โ Scribed by Daniel L. Comins; Jack D. Brown
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 180 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Titanium enolates add to the 4-position of l-phenoxycarbonylpyridinium salts to give 1,4_dihydropyridines; subsequent aromatization provides 4-(2-oxoalkyl)pyridines. Development of practical methods for directing nucleophiles to the 4-position of a pyridine ring has been a challenge to synthetic chemists for many years. We and the research groups of Lylel, Piers2, Katritzky3, and Akiba4 have made recent
๐ SIMILAR VOLUMES
An efficient method to synthesize 1-P-keto substituted 2-ethoxycarbonyl ( or 2-acetyl )-1, 2-dihydroisoquinolines (A) is described, utilizing boron enolates and isoquinolinium salts. The products were treated with sodium ethoxide to afford