Direct synthesis of monofunctionalized indolizine derivatives bearing alkoxymethyl substituents at C-3 and their benzofused analogues.
[reaction: see text] Treatment of (Z)-2-pyridine and quinoline silylated vinylacetylenes at reflux with several alcohols in the presence of a suitable inorganic base (KOH, K2CO3, CsF, or KF) serendipitously gave 3-alkoxylmethylindolizines and the corresponding 1-alkoxymethylpyrrolo [1,2-a]quinolines and not the anticipated desilylated vinylacetylene derivatives. A mechanistic possibility for this unexpected chemical transformation is suggested.
Kaloko
Joseph
J
Department of Chemistry, Thomas Harriot College of Arts and Sciences, East Carolina University, Science and Technology Building, Suite 300, Greenville, North Carolina 27858-4343, USA.
Hayford
Anthony
A
D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure
D007212:Indolizines; C035094:indolizine; D002244:Carbon; D001554:Benzene