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Direct Synthesis of Monofunctionalized Indolizine Derivatives Bearing Alkoxymethyl Substituents at C-3 and Their Benzofused Analogues

2005; American Chemical Society; Volume: 7; Issue: 19 Linguagem: Inglês

10.1021/ol051860t

1523-7060

Joseph Jr. Kaloko, Anthony Hayford,

Synthesis and Characterization of Pyrroles

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.