Journal of Organic Chemistry p. 2740 - 2744 (1988)
Update date:2022-08-04
Topics: Functionalization Metalation Heterocyclic
Estel, L.
Marsais, F.
Queguiner, G.
Lithiation, iodination, and fluorine substitution on 2-fluoropyridine gave 2-substituted 3-iodopyridines, which were further subjected to iodine SRN1 substitution by carbon, sulfur, and phosphorus nucleophiles.Iodine substitution by enolates on 2-amino-3-iodopyridines afforded ketones, which were further cyclized to various 1,2-disubstituted pyrrolo<2,3-b>pyridines. 2-Amino-3-iodo-, 3-amino-4-iodo, and 4-amino-3-iodopyridines were prepared by directed metalation of 2-, 3-, and 4-(pivaloylamino)pyridines.Substitution of iodine by enolates under SRN1 conditions and acidic cyclization led to various 2-substituted pyrrolo<2,3-b>, -<2,3-c>-, and -<3,2-c>pyridines in high yields.
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