Title of article :
A Simple and Efficient Method for the Synthesis of 2,3,5,6-Tetrachloro-4- iodopyridine, and its Reactivity Toward Hard and Soft Nucleophiles
Author/Authors :
Ranjbar-Karimi, Reza Department of Chemistry - Faculty of Science - Vali-e-Asr University , Davoodian, Tayebeh Department of Chemistry - Faculty of Science - Vali-e-Asr University , Poorfreidoni, Alireza Department of Chemistry - Faculty of Science - Vali-e-Asr University , Mehrabi, Hossein Department of Chemistry - Faculty of Science - Vali-e-Asr University
Abstract :
2,3,5,6-tetrachloro-4-iodopyridine was successfully synthesized in one-step from the reaction of pentachloropyridine with sodium iodide using microwave irradiation. The reaction of O, N, and S centered nucleophiles with 2,3,5,6-tetrachloro-4-iodopyridine was studied in order to assess regiochemistry of aromatic nucleophilic substitution. Substitution occurs at the para position to ring nitrogen by S centered nucleophiles, while O and N centered nucleophiles substitution occurs at the ortho position of pyridine ring. IR, 1H NMR, and 13C NMR spectroscopy, confirmed the structures of all the compounds.
Keywords :
Pentachloropyridine , Tetrachloro-4-iodopyridine , Regiochemistry , Microwave , Heterocycle
