Synthesis of symmetrical and unsymmetrical ureas using unsymmetrical diaryl carbonates

Synthetic Communications

Volumn 26, Issue 2, 1996, Pages 331-349

  Freer, Richard ^a   McKillop, Alexander ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

UREA DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030044040     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003622     Document Type: Article

References (9)

1. Sandler, S.R.; Karo, W. "Organic Functional Group Preparations", Academic Press, New York, 1971, Vol. II, 135-165.
2. Izdebski, J.; Pawlak, D. Synthesis 1989, 423-425.
3. Majer, P.; Randad, R.S. J. Org. Chem. 1994, 59, 1937-1938.
4. Hegarty, A.F. in "Comprehensive Organic Chemistry", Barton, D.H.R.; Ollis, W.D. Eds., Pergamon Press, Oxford, 1979, Vol. 2, 1084; one possible explanation is that the second (tertiary) basic centre in (6) induces facile conversion to the isocyanates RNCO, the ease of this transformation reflecting the relative basicities of the amines (2)-(4).
5. Barcelo, G.; Senet, J.-P.; Sennyey, G.; Bensoam, J.; Loffet, A. Synthesis 1986, 627-632.
6. Gresser, M.J.; Jenks, W.P. J. Am. Chem. Soc. 1977, 99, 6963-6970.
7. Brown, P.; Djerassi, C. J. Am. Chem. Soc. 1967, 89, 2711-2719.
8. Carbamates (10c, e) and (12) were not isolated and characterised.
9. Weygand, F.; Mitgau, R. Chem. Ber. 1955, 88, 301-308.