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Regioselectivity, scope, and limitations of the addition of organolithium and allylmagnesium reagents to 1H-pyridine-2-thiones; access to 3,4-, 3,6-, and 5,6-dihydropyridine-2-thiones

Regioselectivity, scope, and limitations of the addition of organolithium and allylmagnesium reagents to 1H-pyridine-2-thiones; access to 3,4-, 3,6-, and 5,6-dihydropyridine-2-thiones

Tetrahedron 63(48): 11862-11877

Organolithium and lithium allyldibutylmagnesate reagents add to readily available NH, NMe, NBn, and NPh substituted pyridine-2-thiones yielding 4-and/or 6-substituted 3,4-or 3,6-dihydropyridine-2-thiones, respectively. The regioselectivity of the addition is dependent on the solvent, temperature, substituent at the nitrogen, and the type or organometallic reactant used, and allows tailoring of both systems. A simple conversion of 6-substituted beta,gamma-unsaturated delta-thiolactams into their alpha,beta-unsaturated isomers makes the above processes a highly versatile synthetic methodology to access 6-substituted 5,6-dihydropyridine-2-thiones-valuable Michael acceptors.

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Accession: 021658521

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DOI: 10.1016/j.tet.2007.09.029

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