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A Quick Route for the Synthesis of 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-ones
Corresponding Author(s) : Arif Ali Khan
Asian Journal of Chemistry,
Vol. 25 No. 8 (2013): Vol 25 Issue 8
Abstract
N-(2-Hydroxy)-benzyl-arylamines (1) gave substantially pure 3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-one 2 on cyclization with carbonyldiimidazole in DMSO in 20-30 min at 20-25 ºC in excellent yields.
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- B.K. Banik, S. Samajdar and I. Banik, Tetrahedron Lett., 44, 1699 (2003).
- V.N. Yuskovets and B.A. Ivin, Tetrahedron Lett., 44, 5279 (2003).
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- J.R. Manning and H.M.L. Davies, Tetrahedron, 64, 6901 (2008).
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References
B.K. Banik, S. Samajdar and I. Banik, Tetrahedron Lett., 44, 1699 (2003).
V.N. Yuskovets and B.A. Ivin, Tetrahedron Lett., 44, 5279 (2003).
J.D. Butler, D.M. Solano, L.I. Robins, M.J. Haddadin and M.J. Kurth, J. Org. Chem., 73, 234 (2008).
R. Pedrosa, C. Andrés, P. Mendiguchía and J. Nieto, J. Org. Chem., 71, 8854 (2006).
H. Cao, H.-F. Jiang, C.-R. Qi, W.-J. Yao and H.-J. Chen, Tetrahedron Lett., 50, 1209 (2009).
J.R. Manning and H.M.L. Davies, Tetrahedron, 64, 6901 (2008).
Y. Tabuchi, Y. Ando, H. Kanemura, I. Kawasaki, T. Ohishi, M. Koida, R. Fukuyama, H. Nakamuta, S. Ohta, K. Nishide and Y. Ohishi, Bioorg. Med. Chem., 17, 3959 (2009).
A.I. Vovk,A.M. Shivanyuk, R.V. Bugas, O.V. Muzychka and A.K. Melnyk, Bioorg. Med. Chem. Lett., 19, 1314 (2009).
S. Wang, Y. Li, Y. Liu, A. Lu and Q. You, Bioorg. Med. Chem. Lett., 18, 4095 (2008).
X. Li, U.H. Manjunatha, M.B. Goodwin, J.E. Knox, C.A. Lipinski, T.H. Keller, C.E. Barry III and C.S. Dowd, Bioorg. Med. Chem. Lett., 18, 2256 (2008).
H. Kai, Y. Morioka, Y. Koriyama, K. Okamoto, Y. Hasegawa, M. Hattori, K. Koike, H. Chiba, S. Shinohara, Y. Iwamoto, K. Takahashi and N. Tanimoto, Bioorg. Med. Chem. Lett., 18, 6444 (2008).
S.D. Young, S.F. Britcher, L.S. Payne, L.O. Tran and W.C. Jr. Lumma, US-5519021 (1996).
M. Patel, S.S. Ko, R.J. Jr. McHugh, J.A. Markwalder, A.S. Srivastava, B.C. Cordova, R.M. Klabe, S. Erickson-Viitanen, G.L. Trainor and S.P. Seitz, Bioorg. Med. Chem. Lett., 9, 2805 (1999).
M. Patel, R.J. Jr. McHugh, B.C. Cordova, R.M. Klabe, S. EricksonViitanen, G.L. Trainor and S.S. Koo, Bioorg. Med. Chem. Lett., 9, 3221 (1999).
A. Klasek, K. Koristek, J. Polis and J. Kosmrlj, Tetrahedron, 56, 1551 (2000).
J. Mindl, O. Hrabik, V. Sterba and J. Kavalek, Coll. Czech. Chem. Commun., 65, 1262 (2000).
L.D.S. Yadav and R. Kapoor, J. Org. Chem., 69, 8118 (2004).
H.A. Staab, Angew. Chem. (Int. Ed. Eng.), 1, 351 (1962).
R.K. Sharma, Synlett, 3073 (2007).
J.K. Seydel, K.J. Schaper, E. Wempe and H.P. Cordes, J. Med. Chem., 19, 483 (1976).
N. Ueyama, T. Yanagisawa, T. Kawai, M. Sonegawa, H. Baba, S. Mochizuki, K. Kosakai and T. Tomiyama, Chem. Pharm. Bull., 42, 1841 (1994).
A.K. Kumar, L.K.M. Rai, K.B. Umesha, Indian J. Heterocycl. Chem., 10, 79 (2000).
R.N. Ram and A.A. Khan, Synth. Commun., 31, 841 (2001).
D.K. Shukla, Synlett, 1859 (2009).
S.J. Joglekar and S.D. Samant, J. Indian Chem. Soc., 65, 110 (1988).