Synthesis and physical properties of the six furylpyridines

Abstract

PIERRE RIBEREAU and GUY QUEGUINER. Can. J. Chem. 61, 334 (1983). The 3-step synthesis of furylpyridines is described, using ethyl pyridinoylacetates as starting materials for 2-fury1 compounds and chloroacetylpyridines for 3-furyl isomers. Furthermore, thcsc last compounds were prepared by a convenient new method for 3-substituted furan synthesis. This synthesis starts from bromopyridines and proceeds through the key intermediates (2.2-diethoxyacetyl)pyridines and methyl 2-(.r-pyridyl)-4,4-diethoxy-2-methoxy-2-butenoates. The physical properties of the furylpyridines have been determined. Structures and interactions between furan and pyridine rings have been discussed by comparing their uv spectra, basicity constants, and dipole moments with those of phenyl and thienylpyriclines.

Synthesis and characterization of novel substituted pyrrole, thiophene and furans

“…Over the last few years, the application of such polymers to flexible, light and small electronic and optical devices have been actively carried out. [13][14][15] Despite a large number of studies, [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] which comprise polymeric heterocyclic systems such as imidazolyl-, thiazolyl-, or quinolylpyrroles, thiophenes or furans, there is no work about the synthesis and properties of these simple linked two ring systems in the literature. Several methods are available for the synthesis of two ring systems, which contain the pyrrole, thiophene or furan ring linked to an imidazole, thiazole, or quinoline ring.…”

Chloride–hydrogen interactions of picolinic, nicotinic and isonicotinic acid chloride hydrochlorides in the crystalline state

“…The acid chloride hydrochlorides of the pyridinecarboxylic acids have been synthesized before, 11 but until now the crystal structures have remained unpresented. A reason for this may be found from the lability of these compounds.…”

Process Development and Multikilogram-Scale Synthesis of a TRPV1 Antagonist

“…The coupling of 9 and 10 to prepare glyoxal 2 proceeded via halogen–metal exchange of 9 (Scheme ), which proved challenging. There are several examples of acylation reactions of this type using organolithium reagents derived from 2-bromopyridines. , The lithiation of 2-bromo-3-(trifluoromethyl)pyridine and the magnesium–halogen exchange of 2-iodo-5-cyanopyridine are also outlined in the literature. When we applied these conditions to our system, we found that proton transfer from the amide was a significant issue, as only modest yields of 2 were observed.…”

“…13 C NMR (400 MHz, CDCl 3 ): δ 159.8, 147.8 (q, J = 5 Hz), 144.1, 121.8 (q, J = 32 Hz), 121.3 (q, J = 272 Hz), 62. 8 6-Bromo-5-trifluoromethylnicotinonitrile (7). 2-Hydroxy-3trifluoromethyl-5-iodopyridine (5) (12.33 kg, 42.67 mol) and copper(I) cyanide (4.01 kg, 44.80 mol) were heated at 120 °C in DMF (52 kg) for 16 h. The batch was then cooled to ambient temperature and filtered through a closed filter to remove copper(I) iodide, and the cake was washed with DMF (11 kg).…”