Reaction of aldimine anions with vinamidinium chloride: three-component access to 3-alkylpyridines and 3-alkylpyridinium salts and access to 2-alkyl glutaconaldehyde derivatives.
N-tert-Butylimino derivatives of aldehydes were deprotonated with LDA and reacted with vinamidinium chloride to give 2-alkylaminopentadienimine derivatives, which were isolated as their corresponding hydrochloride in 68-81% yield. Reaction of these derivatives with ammonium acetate or salts of primary amines, in n-butanol at 80 degrees C, afforded the corresponding 3-alkylpyridines or 3-alkylpyridinium salts in high yield. Alkaline hydrolysis of 2-alkylaminopentadieneimine derivatives allowed a practical accesss to potassium salts of 2-alkylglutaconaldehyde.
Wypych
Jean-Charles
JC
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Nguyen
Tuan Minh
TM
Bénéchie
Michel
M
Marazano
Christian
C
D000447:Aldehydes / Q000737:chemistry*; D000468:Alkalies; D000478:Alkylation; D000586:Amination; D000818:Animals; D000838:Anions / Q000737:chemistry; D003500:Cyclization; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007097:Imines / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000737:chemistry
D000447:Aldehydes; D000468:Alkalies; D000838:Anions; D007097:Imines; D011725:Pyridines; C058716:catharinine; D014747:Vinblastine; C007860:glutaconaldehyde