First Example of Lewis Acid Catalyzed 3-Substituted 5-Arylidene-1-methyl-2-thiohydantoin Formation

Brian T. Gregg; William G. Earley; Kathryn C. Golden; John F. Quinn; Dana A. Razzano; W. Martin Rennells

doi:10.1055/s-2006-950342

PAPER

First Example of Lewis Acid Catalyzed 3-Substituted 5-Arylidene-1-methyl-2-thiohydantoin Formation

Brian T. Gregg*, William G. Earley, Kathryn C. Golden, John F. Quinn, Dana A. Razzano, W. Martin Rennells
Albany Molecular Research, Inc., 21 Corporate Circle, PO Box 15098, Albany, NY 12212-5098, USA
Fax: +1(518)8674381; e-Mail: brian@albmolecular.com;

Abstract

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Abstract

A survey of Lewis acids was conducted to facilitate the formation of arylidenethiohydantoins. The use of indium(III) triflate shows significant advantages in facilitating this reaction. In most examples, the Lewis acid promoted catalysis gave shorter reaction times, higher conversion, and better purity profiles as compared to the traditional uncatalyzed reactions.

Key words

Lewis acids - catalysis - heterocycles - indium - condensation

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References

1 Kiec-Kononowicz K. Szymanska E. Farmaco 2002, 57: 909

2 Khodair AI. El-Barbary AA. Abbas YA. Imam DR. Phosphorous, Sulfur Silicon Relat. Elem. 2001, 170: 261

3 Mehta N. Risiger CA. Soroko FE. J. Med. Chem. 1981, 24: 465

4 Khodair AI. Nielsen J. Heterocycles 2002, 57: 1017

5a Villemin D. Martin M. Synth. Commun. 1998, 28: 3201

5b Bramson HN. Corona J. Davis ST. Dickerson SH. Edelstein M. Frye SV. Gampe RT. Harris PA. Hassell A. Holmes WD. Hunter RN. Lackey KE. Lovejoy B. Luzzio MJ. Montana V. Roque WJ. Rusnak D. Shewchuk L. Veal JM. Walker DH. Kuyper LF. J. Med. Chem. 2001, 44: 4339

5c Sun L. Liang C. Shirazian S. Zhou Y. Miller T. Cui J. Fukuda JY. Chu J.-Y. Nematalla A. Wang X. Chen H. Sistla A. Luu TC. Tang F. Wei J. Tang C. J. Med. Chem. 2003, 46: 1116

5d Thompson AM. Delaney AM. Hamby JM. Schroeder MC. Spoon TA. Crean SM. Showalter HDH. Denny WA. J. Med. Chem. 2005, 48: 4628

6 Deng G. Tiegan R. Synth. Commun. 2003, 33: 2995

7 Zheng X. Zhang Y. Synth. Commun. 2003, 33: 161

8 Villemin D. Martin B. Garrigues B. Synth. Commun. 1993, 23: 2251

9 Msaddek M. Rammah M. Ciamala K. Vebrel J. Laude B. Synthesis 1997, 1495

10 Sun J. Chao-Guo Y. Han Y. Synth. Commun. 2001, 31: 151

11 Muxfeldt H. Behling J. Grethe G. Rogalski W. J. Am. Chem. Soc. 1967, 89: 4991

12a Cook AH. Cox SF. J. Chem. Soc. 1949, 2342

12b Hassan E. Sulkowski TS. Abou-Gharbia M. Butera JA. Chai S.-Y. McFarlane GR. McKean M.-L. Babiak JL. Adelman SJ. Quinet EM. J. Med. Chem. 2004, 47: 681