R. Erenler, J. Biellmann
Feb 1, 2007
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0
Influential Citations
2
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Journal
Journal of The Chinese Chemical Society
Abstract
dienyl)pyridine 11 and 3-(3-(pyridine-3-yl)propa-1,2-dienyl)pyridine 17 and the acetylenes 5, 12 and 16 wereobtainedbyreductionofthecorrespondingpropargylicacetates 3, 10and 15bySamarium(II)iodide in the presence of Pd(0). Base-promoted isomerisation of acetylene 12 provided allene 11 in a yield of 80%. 1-(Pentafluorophenyl)-3-phenylprop-2-yn-1-ol 2 was prepared from phenylacetylene and pentafluorobenzaldehyde. The condensation of nicotinaldehyde with trimethylsilylacetylene gave the 3-(trimethylsilyl)-1-(pyridine-3-yl)prop-2-yn-1-ol 7. The removal of the silyl group of 7 to acetylene 8 was done in basic conditions. The Pd catalysed condensation of the acetylene 8 with iodobenzene gave 3-phenyl-1-(pyridine-3-yl)prop-2-yn-1-ol 9. The Pd catalysed condensation of 8 with 3-bromopyridine gave the 1,3-dipyridin-3-yl-prop-2-yn-1-ol 14. The propargylic alcohols 2, 9 and 14were converted to the acetates 3, 10 and 15 with acetic anhydride-pyridine.