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One Pot Synthesis of Hetero/Aryl-Urea Derivatives: Chlorosulfonyl Isocyanate, in situ Hydrolysis Method
Corresponding Author(s) : A. Panasa Reddy
Asian Journal of Chemistry,
Vol. 25 No. 3 (2013): Vol 25 Issue 3
Abstract
An interesting approach for the direct and general synthesis of primary hetero/aryl urea compounds from corresponding amines. The highly efficient synthesis of mono-substituted hetero-aryl urea compounds by using chlorosulfonyl isocyanate followed by hydrolysis provides the corresponding urea in high yield and purity in reliable reaction conditions. Total 13 derivatives (4a-4m) were successfully synthesized by this approach and characterized. These were more interesting as further preparation of more cyclized compounds in use of drug and agro discoveries.
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- D.J. Kempf, K.C. Marsh, D.A. Paul, M.F. Knigge, D.W. Norbeck, W.E. Kohlbrenner, L. Codacovi, S. Vasavanonda, P. Bryant and X.C. Wang, Antimicrob. Agents Chemother., 35, 2209 (1991).
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- T.P. Vyshnyakova, I.A. Golubeva and E.V. Glebova, Russ. Chem. Rev. (Engl. Trans.), 54, 249 (1985).
- P. Majer and R.S. Randad, J. Org. Chem., 49, 1937 (1994).
- N. Sonoda, T. Yasuhara, K. Kondo, T. Ikeda and S. Tsutsumi, J. Am. Chem. Soc., 93, 6344 (1971).
- R.A. Franz and F. Applegath, J. Org. Chem., 26, 3304 (1961).
- A. Nefzi, N.A. Ong and R.A. Houghten, Tetrahedron Lett., 41, 5441 (2000).
- J.E. McCusker, A.D. Main, K.S. Johnson, C.A. Grasso and L. McElweeWhite, J. Org. Chem., 65, 5216 (2000); (b) I. Maya, O. Lopez, S. Maza, J.G. Fernandez-Bolanos and J. Fuentes, Tetrahedron Lett., 44, 8539 (2003).
- Q. Liu, N.W. Luedtke and Y. Tor, Tetrahedron Lett., 42, 1445 (2001).
- D. Saylick, M.J. Horwath, P.S. Elmes and WR. Jackson, J. Org. Chem. Soc., 64, 3940 (1999).
- S. Porwanski, S. Menuel, X. Marsura and A. Marsura, Tetrahedron Lett., 45, 5027 (2004).
References
D.J. Kempf, K.C. Marsh, D.A. Paul, M.F. Knigge, D.W. Norbeck, W.E. Kohlbrenner, L. Codacovi, S. Vasavanonda, P. Bryant and X.C. Wang, Antimicrob. Agents Chemother., 35, 2209 (1991).
J. Gante, Synthesis, 405 (1989).
A. Tsopmo, D. Ngnokam, D. Ngamga, J.F. Ayafor and O. Sterner, J. Nat. Prod., 62, 1435 (1999); (b) Y. Funabashi, S. Tsubotani, K. Koyama, N. Katayama and S. Harada, Tetrahedron, 49, 13 (1993).
T.P. Vyshnyakova, I.A. Golubeva and E.V. Glebova, Russ. Chem. Rev. (Engl. Trans.), 54, 249 (1985).
P. Majer and R.S. Randad, J. Org. Chem., 49, 1937 (1994).
N. Sonoda, T. Yasuhara, K. Kondo, T. Ikeda and S. Tsutsumi, J. Am. Chem. Soc., 93, 6344 (1971).
R.A. Franz and F. Applegath, J. Org. Chem., 26, 3304 (1961).
A. Nefzi, N.A. Ong and R.A. Houghten, Tetrahedron Lett., 41, 5441 (2000).
J.E. McCusker, A.D. Main, K.S. Johnson, C.A. Grasso and L. McElweeWhite, J. Org. Chem., 65, 5216 (2000); (b) I. Maya, O. Lopez, S. Maza, J.G. Fernandez-Bolanos and J. Fuentes, Tetrahedron Lett., 44, 8539 (2003).
Q. Liu, N.W. Luedtke and Y. Tor, Tetrahedron Lett., 42, 1445 (2001).
D. Saylick, M.J. Horwath, P.S. Elmes and WR. Jackson, J. Org. Chem. Soc., 64, 3940 (1999).
S. Porwanski, S. Menuel, X. Marsura and A. Marsura, Tetrahedron Lett., 45, 5027 (2004).