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Synthesis 2008(3): 417-424  
DOI: 10.1055/s-2008-1032024
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Michael Carboni, Jean-Marie Gomis, Olivier Loreau*, Frédéric Taran*
Service de Chimie Bioorganique et de Marquage (SCBM), Institut de Biologie et de Technologies de Saclay (IBITECS), Direction des Sciences du Vivant (DSV), Commissariat à l’Energie Atomique (CEA), Gif-sur-Yvette 91191, France
Fax: +33(1)69087991; e-Mail: frederic.taran@cea.fr;
Further Information

Publication History

Received 15 October 2007
Publication Date:
10 January 2008 (online)

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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

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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 Å3; Z = 4; Dcalc = 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.