Sulfur Mediated Ritter Reactions: The Synthesis of Cyclic Amides

Abstract

Simple β-hydroxy-γ-phenylsulfanyl nitriles undergo a selective Ritter reaction, onto a thiiranium (episulfonium) ion, to yield 15-membered triamides. This selective trimerisation allows the rapid synthesis of these macrocylic triamides.

Keywords

amides - sulfur - Ritter reaction - macrocycles - ring closure - thiiranium Ions

References

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16

Crystallographic data for the syn-amide 24: C₁₂H₁₇NOS, Monoclinic, space group P2(1)/c. a = 15.6767(9) Å, b = 8.9827(6) Å, c = 18.7004(11) Å, β = 107.086(4)°, V = 2517.1(3) ų, Z = 8, D_c = 1.179 Mg/m³, µ = 0.233mm^-1, F(000) = 960, Data (12949 reflections collected, 3269 independent reflections R_int = 0.0793) were measured on a Nonius Kappa CCD diffractometer at 180(2) K. Refinement Method Full-matrix least-squares on F², [R₁ = 0.1021 (I >2σI), ωR₂ = 0.2183], Goodness-of-fit on F² 1.038. The crystals were small and of poor quality, hence the relatively high R-factors.