Oxidative cyclization of 2-pyrrolidinyl-acetamide and 2-pyrrolidinyl-propionamide local anaesthetics

Autor: L. Vasvari-Debreczy, A.H. Beckett, W. Vutthikongsirigool
Rok vydání: 1981
Předmět:
Zdroj: Tetrahedron. 37:4337-4342
ISSN: 0040-4020
DOI: 10.1016/0040-4020(81)85031-4
Popis: 2 - Pyrrolidinyl - acetamide and -propionamide local anaesthetics (1a–d) on oxidation with mercuric acetate, potassium hexacyanoferrate(III) and potassium permanganate underwent oxidative cyclization to give new bicyclic compounds, hexahydro - 1H - pyrrolo[1,2 - a]imidazolin - 2 - ones (2a–d). The propionamides (1c–d) yielded mixtures of the two possible diastereoisomers of 2c and 2d. These were separated; in solution and above their melting points they epimerized via ring opening and reclosure between the 7a-carbon and 1-nitrogen atoms.
Databáze: OpenAIRE