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Volumn 32, Issue 2, 2011, Pages 716-718

An efficient hydration of cyanamides to substituted ureas with acetaldoxime as an effective water surrogate

Author keywords

Acetaldoxime; Cyanamides; Hydration; Ureas; Water surrogate

Indexed keywords


EID: 79951938595     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.2.716     Document Type: Article
Times cited : (18)

References (40)
  • 5
    • 14544273218 scopus 로고    scopus 로고
    • and further references cited therein
    • (a) Moorthy, J. N.; Singhal, N. J. Org. Chem. 2005, 70, 1926-1929 and further references cited therein.
    • (2005) Org. Chem. , vol.70 , pp. 1926-1929
    • Moorthy, J.N.1    Singhal, N.J.2
  • 11
    • 76449085093 scopus 로고    scopus 로고
    • For the hydration of nitriles to amides with the aid of acetaldoxime, see:
    • For the hydration of nitriles to amides with the aid of acetaldoxime, see: (a) Kim, E. S.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 1589-1591.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 1589-1591
    • Kim, E.S.1    Lee, H.S.2    Kim, S.H.3    Kim, J.N.4
  • 14
    • 72849113087 scopus 로고    scopus 로고
    • Chang and co-workers reported an efficient Rh-catalyzed conversion of aldoxime to amide, with a nitrile additive for the rate acceleration. Activated nitrile by Rh catalyst played an important role in the conversion, see
    • (d) Lee, J.; Kim, M.; Chang, S.; Lee, H.-Y. Org. Lett. 2009, 11, 5598-5601. Chang and co-workers reported an efficient Rh-catalyzed conversion of aldoxime to amide, with a nitrile additive for the rate acceleration. Activated nitrile by Rh catalyst played an important role in the conversion, see.
    • (2009) Org. Lett. , vol.11 , pp. 5598-5601
    • Lee, J.1    Kim, M.2    Chang, S.3    Lee, H.-Y.4
  • 22
    • 26444545414 scopus 로고    scopus 로고
    • For the hydration of cyanamide to urea via a neighboring group participation
    • For the hydration of cyanamide to urea via a neighboring group participation, see: (a) Snider, B. B.; Duvall, J. R. Org. Lett. 2005, 7, 4519-4522.
    • (2005) Org. Lett. , vol.7 , pp. 4519-4522
    • Snider, B.B.1    Duvall, J.R.2
  • 25
    • 36749005584 scopus 로고    scopus 로고
    • For the general synthesis of urea derivatives, and further references cited therein
    • For the general synthesis of urea derivatives, see: (a) Artuso, E.; Degani, I.; Fochi, R.; Magistris, C. Synthesis 2007, 3497-3506 and further references cited therein.
    • (2007) Synthesis , pp. 3497-3506
    • Artuso, E.1    Degani, I.2    Fochi, R.3    Magistris, C.4
  • 27
    • 33744497565 scopus 로고    scopus 로고
    • and further references cited therein
    • (c) Peng, X.; Li, F.; Xia, C. Synlett 2006, 1161-1164 and further references cited therein.
    • (2006) Synlett , pp. 1161-1164
    • Peng, X.1    Li, F.2    Xia, C.3
  • 32
    • 0031774549 scopus 로고    scopus 로고
    • For the synthesis of cyanamides
    • For the synthesis of cyanamides, see: (a) Kaupp, G.; Schmeyers, J.; Boy, J. Chem. Eur. J. 1998, 4, 2467-2474.
    • (1998) Chem. Eur. J. , vol.4 , pp. 2467-2474
    • Kaupp, G.1    Schmeyers, J.2    Boy, J.3
  • 39
    • 79951874093 scopus 로고    scopus 로고
    • 3 (3 mol%) afforded 2a in 91% yield
    • The reaction of 1a in aqueous EtOH did not produce 2a even in the presence of acetaldoxime, and the reason is not clear at this stage. The hydration of cyanamide can be performed under solvent-free conditions. As an example, the reaction of 1a and acetaldoxime (3.0 equiv) at room temperature in the presence of InCl3 (3 mol%) afforded 2a in 91% yield.


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