56159-20-7Relevant articles and documents
THE REACTION OF 4-CHLOROPYRIDINE 1-OXIDES WITH ACTIVATED ACETYLENES. A CONVENIENT ONE-STEP SYNTHESIS OF FUROPYRIDINES
Abramovitch, Rudolph A.,Deeb, Ali,Kishore, Dharma,Mpango, George B. W.,Shinkai, Ishiro
, p. 167 - 172 (2007/10/02)
The reaction of 4-chloro- and 4-pseudohalogeno-pyridine 1-oxides with activated acetylenes (phenylcyanoacetylene, methyl phenylpropiolate, phenylpropiolaldehyde, methyl propiolate, and ethynyl p-tolyl sulphone) gave good yields of substituted furopyridines 7.With 1-phenyl-2-methanesulphonylacetylene under mild conditions the initial -shift product 9 was isolated and converted to 7 with base.The structure of 7 was established unambiguously by using Eu(fod)3-induced NMR shifts.The mechanism of the reaction is discussed briefly and consecutive -shifts are proposed to account for the formation 7.