Pyridinium ylides in the one-pot synthesis of a new quinoline/indolizine hybrid
The reaction of 1-(quinolin-2-ylmethyl)pyridinium ylide with dimethyl acetylenedicarboxylate was investigated. The X-ray crystallographic characterization of the new dimethyl 3-(quinolin-2-yl)indolizine-1,2-dicarboxylate (2) shows the formation of a five-membered ring between the pyridine ring and the methylene group.
Titel compounds can be obtained either by condensation of chinolinaldehyds with aminoguanidins in a ethanol/water mixture in the presens of Protones (way A), or starting with chinaldines via aniles or nitrones and reaction with aminoguanidinsalts (way B).Way B has any advantages and is described by examples.