Novel two-step, one-pot synthesis of primary acylureas

Tetrahedron Letters

Volumn 51, Issue 44, 2010, Pages 5843-5844

  Xiao, Zili ^a   Yang, Michael G ^a   Tebben, Andrew J ^a   Galella, Michael A ^a   Weinstein, David S ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYANAMIDE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77957574529     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.003     Document Type: Article

References (7)

1. Computer modeling and the crystal structure suggest that the trans isomer is the preferred conformation. The initial conformational energies for both rotomers were minimized using the OPLSAA-2005 force field in Macromodel (version 9.7, Schrodinger, LLC, New York, NY, 2009). Ab initio minimized conformations were then generated within Jaguar (version 7.6, Schrodinger, LLC, New York, NY, 2009) at the B3LYP/6-31G level of theory in vacuum. Final energies were calculated using the SM8 solvation model with the M06-2X/6-31 basis set as implemented within Jaguar.
2. T. Maki, K. Ishihara, and H. Yamamoto Synlett 8 2004 1355 1358
3. B. Seiller, D. Heins, C. Bruneau, and P.H. Dixneuf Tetrahedron 51 40 1995 10901 10912
4. E.W. Maynert, and E. Washburn J. Org. Chem. 15 1950 259 261
5. For the synthesis of second and tertiary acylureas see: D. Wodka, M. Robbins, P. Lan, R.L. Martinez, J. Athanasopoulos, and G.M. Makara Tetrahedron Lett. 47 2006 1899
6. For a related study on hydrolysis of N-acylcyanamide see: J. Perronnet, P. Jacques, and L. Taliani J. Heterocycl. Chem. 18 1981 433 435
7. 6) δ ppm: 15.61, 31.37, 127.86, 128.86, 130.01, 138.56, 152.97, 174. 22.