Synthesis of Thiohydantoins by Phosphine-Catalyzed Reaction of Thioureas with Arylpropiolates

Abstract

A simple and efficient method for constructing thiohydantoin heterocycles using a phosphine-catalyzed tandem umpo­lung addition and intramolecular cyclization of thioureas on arylpropiolates is described.

Key words

thioureas - alkynes - catalysis - phosphines

References

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8

Crystal data of compound 2a: C₁₂H₁₂ON₂S, M = 232; T = 293 (2) K, λ = 0.71073 Å; Crystal system = monoclinic; Space group: P 21/n; Unit cell dimensions: a = 12.036 Å, b = 8.065 Å, c = 12.966 Å, α = γ = 90.00°, β = 115.46°; V = 1136.4 ų; Z = 4; D_calc = 1.358 g /cm³; Absorption coefficient: 0.284 mm^-1; F(000) = 488; Crystal size: 0.25 × 0.25 × 0.10 mm; Reflections collected: 9597; Independent reflections: 2604 [R(int) = 0.0283]; Refinement method, full-matrix least-squares on F2; Goodness-of-fit on F2: 1.037; Final R indices [I > 2σ(I)] R1 = 0.0428, wR2 = 0.1052; R indices (all data) R1 = 0.0704, wR2 = 0.1204; Extinction coefficient: 0.033; Largest diff. peak and hole: 0.186 and -0.196e Å^-3.