Abstract
Several new chiral oxazolines were prepared conveniently in good to high yields using a two-step synthesis involving formation of an optically active amide, in situ conversion of the amide into tosylate (OTs) and finally ring closing reaction under MW irradiation (800 W) in solvent free condition. A comparison of these results with those obtained from the ring closing reaction under classical conditions was also made.
Similar content being viewed by others
Refrences
A. Saeed, D.W. Young, Tetrahedron 48 (1992) 2507
J. Shoji, H. Hinoo, T. Haltori, K. Kirooka, Y. Kimura, T. Yoshida, J. Antibiot. 42 (1988) 1460.
X.-M. Zhang, H.-L. Zhang, W.-Q. Lin, L.-Z. Gong, A.- Q. Mi, X. Cui, Y.-Z. Jiang, K.-B. Yu, J. Org. Chem. 68 (2003) 4322.
T.G. Gant, A.I. Meyers, Tetrahedron 50 (1994) 2297
A.K. Ghosh, P. Mathivanan, J. Gappiello, Tetrahedron: Asymmetry 9 (1998) 1.
B.S. Davidson, Chem. Rev. 93 (1993) 1771
J.P. Michael, G. Pattenden, Angew. Chem., Int. Ed. Engl. 32 (1993) 1
H. Sone, H. Kigoshi, K. Yamada, Tetrahedron 53 (1997) 8149
A. Rudi, M. Aknin, E.M. Gaydou, Y. Kashman, Tetrahedron 54 (1998) 13203
C.D.J. Boden, M. Norley, G.J. Pattenden, J. Chem. Soc., Perkin Trans. 1 (2000) 883 and references cited therein.
J.A. Frump, Chem. Rev. 71 (1971) 483.
J.A. Frump, Chem. Rev. 71 (1971) 483
A.I. Meyers, E.D. Mihelich, Angew. Chem., Int. Ed. Engl. 15 (1976) 270
M. Reuman, A.I. Meyers, Tetrahedron 41 (1985) 837
T.G. Gant, A.I. Meyers, Tetrahedron 50 (1994) 2297
D.J. Ager, I. Prakash, D.R. Schaad, Chem. Rev. 96 (1996) 835.
B. Colman, S.E. de Sousa, P. O’Brien, T.D. Towers, W. Watson, Tetrahedron: Asymmetry 10 (1999) 4175 and references cited therein.
J.A. Frump, Chem. Rev. 71 (1971) 483
A.I. Meyers, E.D. Michelich, Angew. Chem. (1976) 321.
R. Sharma, S.K. Vadivel, R.I. Duclos Jr., A. Makriyannis, Tetrahedron Lett. 50 (2009) 5780.
H. Wenker, J. Am. Chem. Soc. 57 (1935) 1079.
H. Vorbruggen, K. Krolikiewicz, Tetrahedron 49 (1993) 9353.
H. Vorbruggen, K. Krolikiewicz, Tetrahedron Lett. 22 (1981) 4471.
K. Kamata, I. Agata, J. Org. Chem. 63 (1998) 3113.
C. Bolm, K. Weickhardt, M. Zehnder, T. Ranff, Chem. Ber. 124 (1991) 1173
D.S. Clarke, R. Wood, Synth. Commun. 26 (1996) 1335.
B. Oussaid, J. Berlan, M. Souflaoui, B. Garrigues, Synth. Commun. 25 (1995) 659.
A.R. Katritzky, C. Cai, K. Suzuki, S.K. Singh, J. Org. Chem. 69 (2004) 811.
P. Wipf, C.P. Miller, Tetrahedron Lett. 33 (1992) 907
P. Wipf, S. Venkatraman, Tetrahedron Lett. 37 (1996) 4659.
A.J. Phillips, Y. Uto, P. Wipf, M.J. Reno, D.R. Williams, Org. Lett. 2 (2000) 1165.
P. Wipf, C.P. Miller, Tetrahedron Lett. 33 (1992) 6267.
M.C. Pirrung, L.N. Tumey, A.L. McClerren, C.R.H. Raetz, J. Am. Chem. Soc. 125 (2003) 1575.
M. Nikpassand, M. Mamaghani, F. Shirini, K. Tabatabaeian, Ultrason. Sonochem. 17 (2010) 301
M. Nikpassand, M. Mamaghani, K. Tabatabaeian, M. Kupaei Abiazi, Mol. Divers. 13 (2009) 389
M. Mamaghani, S. Dastmard, ARKIVOC, ii (2009) 168
K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Catal. Commun. 9 (2008) 416
K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, J. Mol. Catal. A 270 (2007) 112
M. Mamaghani, K. Tabatabaeian, M. Mirzaeinejad, M. Nikpassand, J. Iranian. Chem. Soc. 3 (2006) 89.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mamaghani, M., Mahmoodi, N.O. & Ghasemi, S.F. An efficient synthesis of New chiral oxazolines. JICS 7, 972–977 (2010). https://doi.org/10.1007/BF03246093
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03246093