N,N′-Di-Boc-Substituted Thiourea
as a Novel and Mild Thioacylating Agent Applicable for the Synthesis
of Thiocarbonyl Compounds

Biao-Lin Yin; Zhao-Gui Liu; Jian-Cun Zhang; Zheng-Rong Li

doi:10.1055/s-0029-1219273

PAPER

N,N′-Di-Boc-Substituted Thiourea as a Novel and Mild Thioacylating Agent Applicable for the Synthesis of Thiocarbonyl Compounds

Biao-Lin Yin*^a, Zhao-Gui Liu^b, Jian-Cun Zhang^b, Zheng-Rong Li^a
^a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China
e-Mail: blyin@scut.edu.cn;
^b Guangzhou Institute of Biomedicine & Health, The Chinese Academy of Sciences, Guangzhou International Business Incubator A-3, Guangzhou Science Park, Guangzhou, 510663, P. R. of China

Abstract

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Abstract

Stable and readily available N,N′-di-Boc-substituted thiourea, when activated with trifluoroacetic acid anhydride, was used as a novel thioacylating agent. Through the thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium benzenethiolate, and sodium malonates with N,N′-di-Boc-substituted thiourea, a series of thiocarbonyl compounds were prepared under mild conditions with good chemical selectivity and functional group tolerance.

Key words

N,N′-di-Boc-substituted thiourea - thioacylating agent - thiocarbonyl

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References

<A NAME="RF20309SS-1">1</A> Lee J. Lee J. Kang M. Shin M. Kim J.-M. Kang S.-U. Choi H.-K. Suh Y.-G. Park H.-G. Oh U. Kim H.-D. Park Y.-H. Ha H.-J. Kim Y.-H. Toth A. Wang Y. Tran R. Pearce LV. Lundberg DJ. Blumberg PM. J. Med. Chem. 2003, 46: 3116

<A NAME="RF20309SS-2">2</A> Ranise A. Spallarossa A. Bruno O. Schenone S. Fossa P. Menozzi G. Bondavalli F. Mosti L. Capuano A. Mazzeo F. Falcone G. Filippelli W. Farmaco 2003, 58: 765

<A NAME="RF20309SS-3">3</A> Cunha S. Macedo FC. Costa GAN. Rodrigues MT. Verde RBV. De Souza Neta LC. Vencato I. Lariucci C. Sá FP. Monatsh. Chem. 2007, 138: 511

<A NAME="RF20309SS-4">4</A> Omar A.-MME. Farghaly AM. Hazzai AAB. Eshba NH. Sharabi FM. Daabees TT. J. Pharm. Sci. 1981, 70: 1075

<A NAME="RF20309SS-5">5</A> Krishnamurthy R. Govindaraghavan S. Narayanasamy . J. Pestic. Sci. 1999, 52: 145

<A NAME="RF20309SS-6">6</A> Kochansky J. Cohen CF. J. Agric. Entomol. 1990, 7: 293

<A NAME="RF20309SS-7">7</A> Vosatka V. Capek A. Budesinsky Z. Collect. Czech. Chem. Commun. 1977, 42: 3186

<A NAME="RF20309SS-8">8</A> Hahn H.-G. Rhee HK. Lee CK. Whang KJ. Korean J. Med. Chem. 2000, 10: 66

<A NAME="RF20309SS-9">9</A> Strickley RG. Anderson BD. Pharm. Res. 1993, 10: 1076

<A NAME="RF20309SS-10">10</A> Patil DG. Chedekel MR. J. Org. Chem. 1984, 49: 997

<A NAME="RF20309SS-11">11</A> Kasmi S. Hamelin J. Benhaoua H. Tetrahedron Lett. 1998, 39: 8093

<A NAME="RF20309SS-12A">12a</A> Satyavan S. Synthesis 1978, 803

<A NAME="RF20309SS-12B">12b</A> Mayer R. In Organosulfur Chemistry Janssen MJ. Wiley-Interscience; New York: 1967. p.219

<A NAME="RF20309SS-13">13</A> Wang C. Chen J. Song Q. Li Z. Xi Z. ARKIVOC 2003, (ii): 155

<A NAME="RF20309SS-14">14</A> Staab HA. Walther G. Liebigs Ann. Chem. 1962, 657: 98

<A NAME="RF20309SS-15A">15a</A> Brain CT. Hallett A. Ko SY. J. Org. Chem. 1997, 62: 3808

<A NAME="RF20309SS-15B">15b</A> Brain CT. Hallett A. Ko SY. Tetrahedron Lett. 1998, 39: 127

<A NAME="RF20309SS-16">16</A> Katritzky AR. Witek RM. Rodriguez-Garcia V. Mohapatra PP. Rogers JW. Cusido J. Abdel-Fattah AAA. Steel PJ. J. Org. Chem. 2005, 70: 7866

<A NAME="RF20309SS-17">17</A> Exposito A. Femandez-Suarez M. Iglesias T. Munoz L. Riguera R. J. Org. Chem. 2001, 66: 4206

For examples concerning the activation of the carbonyl group of an amide and its synthetic application, see:

<A NAME="RF20309SS-18A">18a</A> Falmagne JB. Escudero J. Taleb-saharaoui S. Ghosez L. Angew. Chem., Int. Ed. Engl. 1981, 20: 879

<A NAME="RF20309SS-18B">18b</A> Sisti NJ. Fowler FW. Grierson DS. Synlett 1991, 816

<A NAME="RF20309SS-18C">18c</A> Thomas EW. Synthesis 1993, 767

<A NAME="RF20309SS-18D">18d</A> Barbaro G. Battaglia A. Bruno C. Giorgianni P. Guerrini A. J. Org. Chem. 1996, 61: 8480

<A NAME="RF20309SS-18E">18e</A> Sisti NJ. Zeller E. Grierson DS. Fowler FW. J. Org. Chem. 1997, 62: 2093

<A NAME="RF20309SS-18F">18f</A> Charette AB. Chua P. J. Org. Chem. 1998, 63: 908

<A NAME="RF20309SS-18G">18g</A> Charette AB. Chua P. Tetrahedron Lett. 1997, 38: 8499

<A NAME="RF20309SS-18H">18h</A> Charette AB. Chua P. J. Org. Chem. 1998, 63: 908

<A NAME="RF20309SS-18I">18i</A> Charette AB. Chua P. Synlett 1998, 163

<A NAME="RF20309SS-18J">18j</A> Charette AB. Chua P. Tetrahedron Lett. 1998, 39: 245

<A NAME="RF20309SS-18K">18k</A> Charette AB. Grenon M. Tetrahedron Lett. 2000, 41: 1677

<A NAME="RF20309SS-18L">18l</A> Wan Z.-K. Wacharasindhu S. Levins CG. Lin M. Tabei K. Mansour TS. J. Org. Chem. 2007, 72: 10194

<A NAME="RF20309SS-19">19</A> Part of this work was published as a preliminary communication: Yin B. Liu Z. Yi M. Zhang J. Tetrahedron Lett. 2008, 49: 3687