Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides

Tetrahedron Letters

Volumn 46, Issue 13, 2005, Pages 2279-2282

  Kiselyov, Alexander S ^a  

^a CHEMDIV INC   (United States)

Author keywords

Carbene; Isonitrile; N Fluoropyridinium; Picolinamide

Indexed keywords

CARBENOID; FLUORIDE; FLUOROPYRIMIDINE DERIVATIVE; ISONITRILE DERIVATIVE; PICOLINAMIDE; QUINALDIC ACID; QUINOLINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 14744290361     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.010     Document Type: Article

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41. 4), and concentrated. Silica gel chromatography (hexanes) afforded 2-chloropyridines 4. Subsequent elution with hexanes/ether (1:2) furnished 2-pyridylcarboxamides 3 as main products along with varying quantities of 5 (5-7% isolated yields). Alternatively, for p-nitrophenyl isocyanide reaction mixtures, the resulting concentrate was washed with ether, the resultant solid residue was recrystallized from EtOH to afford analytically pure 3i-p. Small amounts of side products (5, 5-8% isolated yields) along with additional quantities of 3 (10-15%) were isolated from the resulting mother liquors by column chromatography on silica gel as described above
42. 5: C, 55.82; H, 3.68; N, 13.95. Found: C, 55.70; H, 3.81; N, 13.81