Reaction of N-fluoropyridinium fluoride with isonitriles and TMSN 3: A convenient one-pot synthesis of tetrazol-5-yl pyridines

Tetrahedron Letters

Volumn 46, Issue 29, 2005, Pages 4851-4854

  Kiselyov, Alexander S ^a  

^a CHEMDIV INC   (United States)

Author keywords

Carbene; Isonitriles; N Fluoropyridinium; Tetrazol 5 yl pyridine; Three component reaction

Indexed keywords

CARBENE; FLUORIDE; ISONITRILE DERIVATIVE; N FLUOROPYRIDINIUM FLUORIDE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; FLUORINATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SYNTHESIS;

EID: 20444476254     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.066     Document Type: Article

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19. 4), and concentrated. Elution with hexanes/EtOAc (1:2) furnished 2-tetrazol-5-yl pyridines 3 as main products along with varying quantities of 4 (6-33%) and 5 (7-10% isolated yields). Alternatively, for p-trifluoromethylphenyl isocyanide reaction mixtures, the resulting concentrate was washed with EtOAc-Et2O, 1:2 (2 × 15 mL), the resultant solid residue was recrystallized from EtOH to afford analytically pure 3i-p.
20. 5: C, 59.83; H, 2.95; N, 20.54. Found: C, 59.58; H, 3.11; N, 20.33.