title: Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates.
abstract: An isothiourea-catalyzed Michael addition-lactamization followed by the sulfide oxidation-elimination/N- to O-sulfonyl transfer sequence for the formation of 2,3,5- and 2,3-substituted pyridine 6-tosylates from (phenylthio)acetic acids and α,β-unsaturated ketimines is described. Incorporation of the valuable 2-sulfonate group allows derivatization to a range of di-, tri-, and tetrasubstituted pyridines.
authors.affiliation: EaStCHEM, School of Chemistry, University of St. Andrews , North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Stark
authors.forename: Timothy J C
authors.initials: TJ
authors.lastname: O'Riordan
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010648:Phenylacetates / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000179:Acrylates; D002264:Carboxylic Acids; D010648:Phenylacetates; D011725:Pyridines; C012577:thiophenyl acetate; D013890:Thiourea; C035956:methyl acrylate