Efficient Solvent-Free Synthesis
of Urea Derivatives Using Selenium-Catalyzed Carbonylation
of Amines with Carbon Monoxide and Oxygen

Takumi Mizuno; Takeo Nakai; Masatoshi Mihara

doi:10.1055/s-0030-1258299

PAPER

Efficient Solvent-Free Synthesis of Urea Derivatives Using Selenium-Catalyzed Carbonylation of Amines with Carbon Monoxide and Oxygen

Takumi Mizuno*, Takeo Nakai, Masatoshi Mihara
Osaka Municipal Technical Research Institute, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan
Fax: +81(6)69638049; e-Mail: tmizuno@omtri.or.jp ;

Abstract

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Abstract

In the presence of a catalytic amount of selenium under ambient pressure of carbon monoxide with oxygen, solvent-free facile synthesis of urea derivatives was developed; the aim is for green and sustainable chemistry. For example, N,N′-dimethylethylenediamine (20 mmol) successfully afforded 1,3-dimethylimidazolidin-2-one (DMI) in 74% yield (1487% based on Se) using selenium catalyst (5 mol%) under mixed gas (CO/O₂, 2:1) at 0.1 MPa, 20 ˚C without any additive or solvent.

Key words

solvent-free - DMI - urea derivatives - carbon monoxide - selenium

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References

1 Merck Index 14th ed.: O’Neil MJ. Heckelman PE. Koch CB. Roman KJ. Merck & Co., Inc.; Whitehouse Station NJ: 2006. p.3249

2 Fieser and Fieser’s Reagents for Organic Synthesis Vol. 11: Fieser M. John Wiley & Sons; New York: 1984. p.207

3 Lo C.-C. Chao P.-M. J. Chem. Ecol. 1990, 16: 3245

4 Mukhopadhyay T. Seebach D. Helv. Chim. Acta 1982, 65: 385

5 Boon WR. J. Chem. Soc. 1947, 307

6 Thomas EW. Nishizawa EE. Zimmermann DC. Williams DJ. J. Med. Chem. 1989, 32: 228

7 Butler AR. Hussain I. J. Chem. Soc., Perkin Trans. 2 1981, 317

8 Dehmlow EV. Rao YR. Synth. Commun. 1988, 18: 487

9 Nomura R. Hasegawa Y. Ishimoto M. Toyosaki T. Matsuda H. J. Org. Chem. 1992, 57: 7339

10 Nomura R. Hasegawa Y. Toyosaki T. Matsuda H. Chem. Express 1992, 7: 569

11 Corriu RJP. Lanneau GF. Mehta VD. J. Organomet. Chem. 1991, 419: 9

12 Paz J. Pérez-Balado C. Iglesias B. Muñoz L. J. Org. Chem. 2010, 75: 3037

13 Malaschichin S. Fu C. Linden A. Heimgartner H. Helv. Chim. Acta 2005, 88: 3253

14 Bogatsky AV. Lukyanenko NG. Kirichenko TI. Synthesis 1982, 464

15 McCusker JE. Grasso CA. Main AD. McElwee-White L. Org. Lett. 1999, 1: 961

16 Mizuno T. Nakai T. Mihara M. Heteroat. Chem. 2009, 20: 64

17 Mizuno T. Mihara M. Nakai T. Iwai T. Ito T. Synthesis 2007, 3135

18 Sonoda N. Yasuhara T. Kondo K. Ikeda T. Tsutsumi S. J. Am. Chem. Soc. 1971, 93: 6344

19 Sonoda N. Pure Appl. Chem. 1993, 65: 699

20 Zhang X. Lu S. Synlett 2005, 10: 1535

21 Kondo K. Sonoda N. Yoshida K. Koishi M. Tsutsumi S. Chem. Lett. 1972, 401

22 Bogatsky AV. Lukyanenko NG. Kirichenko TI. Synthesis 1982, 464

23 Saegusa T. Kobayashi S. Hirota K. Ito Y. Bull. Chem. Soc. Jpn. 1969, 42: 2610