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

 

 Buy Article Permissions and Reprints All articles of this category

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.

References

• 1 Merck Index   14th ed.:  O’Neil MJ. Heckelman PE. Koch CB. Roman KJ. Merck & Co., Inc.; Whitehouse Station NJ: 2006.  p.3249 
  Google Scholar
• 2 Fieser and Fieser’s Reagents for Organic Synthesis   Vol. 11:  Fieser M. John Wiley & Sons; New York: 1984.  p.207 
  Google Scholar
• 3 Lo C.-C. Chao P.-M. J. Chem. Ecol.  1990,  16:  3245 
  CrossrefGoogle Scholar
• 4 Mukhopadhyay T. Seebach D. Helv. Chim. Acta  1982,  65:  385 
  CrossrefGoogle Scholar
• 5 Boon WR. J. Chem. Soc.  1947,  307 
  CrossrefGoogle Scholar
• 6 Thomas EW. Nishizawa EE. Zimmermann DC. Williams DJ. J. Med. Chem.  1989,  32:  228 
  CrossrefGoogle Scholar
• 7 Butler AR. Hussain I. J. Chem. Soc., Perkin Trans. 2  1981,  317 
  CrossrefGoogle Scholar
• 8 Dehmlow EV. Rao YR. Synth. Commun.  1988,  18:  487 
  CrossrefGoogle Scholar
• 9 Nomura R. Hasegawa Y. Ishimoto M. Toyosaki T. Matsuda H. J. Org. Chem.  1992,  57:  7339 
  CrossrefGoogle Scholar
• 10 Nomura R. Hasegawa Y. Toyosaki T. Matsuda H. Chem. Express  1992,  7:  569 
  Google Scholar
• 11 Corriu RJP. Lanneau GF. Mehta VD. J. Organomet. Chem.  1991,  419:  9 
  CrossrefGoogle Scholar
• 12 Paz J. Pérez-Balado C. Iglesias B. Muñoz L. J. Org. Chem.  2010,  75:  3037 
  CrossrefPubMedGoogle Scholar
• 13 Malaschichin S. Fu C. Linden A. Heimgartner H. Helv. Chim. Acta  2005,  88:  3253 
  CrossrefGoogle Scholar
• 14 Bogatsky AV. Lukyanenko NG. Kirichenko TI. Synthesis  1982,  464 
  Article in Thieme ConnectGoogle Scholar
• 15 McCusker JE. Grasso CA. Main AD. McElwee-White L. Org. Lett.  1999,  1:  961 
  CrossrefGoogle Scholar
• 16 Mizuno T. Nakai T. Mihara M. Heteroat. Chem.  2009,  20:  64 
  CrossrefGoogle Scholar
• 17 Mizuno T. Mihara M. Nakai T. Iwai T. Ito T. Synthesis  2007,  3135 
  Article in Thieme ConnectGoogle Scholar
• 18 Sonoda N. Yasuhara T. Kondo K. Ikeda T. Tsutsumi S. J. Am. Chem. Soc.  1971,  93:  6344 
  CrossrefGoogle Scholar
• 19 Sonoda N. Pure Appl. Chem.  1993,  65:  699 
  CrossrefGoogle Scholar
• 20 Zhang X. Lu S. Synlett  2005,  10:  1535 
  Article in Thieme ConnectGoogle Scholar
• 21 Kondo K. Sonoda N. Yoshida K. Koishi M. Tsutsumi S. Chem. Lett.  1972,  401 
  CrossrefGoogle Scholar
• 22 Bogatsky AV. Lukyanenko NG. Kirichenko TI. Synthesis  1982,  464 
  Article in Thieme ConnectGoogle Scholar
• 23 Saegusa T. Kobayashi S. Hirota K. Ito Y. Bull. Chem. Soc. Jpn.  1969,  42:  2610 
  CrossrefGoogle Scholar