Ring-Closing Metathesis Reactions on Azinium Salts: Straightforward Access to Quinolizinium Cations and Their Dihydro Derivatives

Autor: Ana M. Cuadro, Beatriz Abarca, Julio Alvarez-Builla, Ana Nunez, Juan J. Vaquero
Rok vydání: 2009
Předmět:
Zdroj: The Journal of Organic Chemistry. 74:4166-4176
ISSN: 1520-6904
0022-3263
DOI: 10.1021/jo900292b
Popis: The ring-closing metathesis reaction of 1-butenyl-2-vinylpyridinium salts and 2-butenyl-1-vinylpyridinium salts using Grubbs second generation and Hoveyda-Grubbs catalysts proved to be an efficient approach to 3,4-dihydro- and 1,2-dihydroquinolizinium salts and the corresponding quinolizinium derivatives by an improved thermal oxidation in the presence of Pd/C without solvent. A comparative study showed that the quinolizinium system was obtained in better yields through the 3,4-dihydroquinolizinium route, thus allowing the synthesis of quinolizinium derivatives or improvements in the yields of some examples reported previously.
Databáze: OpenAIRE