Abstract
Efficient synthesis of 2-oxazolines by the reaction of nitriles with β-aminoalcohols using InCl3 as catalyst under reflux conditions is reported. This catalyst can be successfully applied to the chemoselective conversion of dicyanobenzenes to their corresponding mono- and bis-oxazolines. The application of ultrasonic and microwave irradiation improved the yields and reduced the reaction times. Another advantage of this catalytic system is its ability to carry out large-scale reactions under ultrasonic and MW irradiations. Alkylnitriles such as acetonitrile was also converted to its corresponding 2-methyloxazoline in the presence of catalytic amounts of InCl3.
Similar content being viewed by others
References
G.W. Zamponi, S.C. Stotz, R.J. Staples, T.M. Andro, J.K. Nelson, V. Hulubei, A. Blumenfeld, N.R. Natale, J. Med. Chem. 46 (2003) 87.
S. Visentin, B. Rolando, A. Di Stilo, R. Frutterro, M. Novara, E. Carbone, C. Roussel, N. Vanthuyne, A. Gasco., J. Med. Chem. 47 (2004) 2688.
A. Zarghi, H. Sadeghi, A. Fassihi, M. Faizi, A. Shafiee, Farmaco 58 (2003) 1077.
R. Peri, S. Padmanabhan, A. Rutledge, S. Singh, D.J. Triggle, J. Med. Chem. 43 (2000) 2906.
P.S. Kharkar, B. Desai, H. Gaveria, B. Varu, R. Loriya, Y. Naliapara, A. Shah, V.M. Kulkarn, J. Med. Chem. 45 (2002) 4858.
G.S. Poindexter, M.A. Bruce, J.G. Breitenbucher, M.A. Higgins, S.-Y. Sit, J.L. Romine, S.W. Martin, S.A. Ward, R.T. McGovern, W. Clarke, J. Russell, I. Antal-Zimanyi, Bioorg. Med. Chem. 12 (2004) 507.
G.S. Poinder, M.A. Bruce, K.L. LeBoulluec, I. Monkovic, S.W. Martin, E.M. Parker, L.G. Iben, R.T. McGovem, A.A. Ortiz, J.A. Stanley, G.K. Mattson, M. Kozlowski, M. Arcuri, I.A. Zimanyi, Bioorg. Med. Chem. Lett. 12 (2002) 379.
Q. Li, K.W. Woods, A. Claiborne, S.L. Gwaltney, K.J. Barr, G. Liu, L. Gehrke, R.B. Credo, Y. Hua Hui, J. Lee, R.B. Warner, P. Kovar, M.A. Nukkala, N.A. Zielinski, S.K. Tahir, M. Fitzgerald, K.H. Kim, K. Marsh, D. Frost, S.C. Ng, S. Rosenberg, H.L. Sham, Bioorg. Med. Chem. Lett. 12 (2002) 465.
T.W. Greene, P.G.M. Wutz, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, New York, 1991.
A.I. Fernańdez, J.M. Fraile, J.I. Garcýá, C.I. Herrerýás, J.A. Mayoral, L. Salvatella, Catal. Commun. 2 (2001) 165.
A.K. Ghosh, P. Mathivanan, J. Cappiello, J. Tetrahedron: Asymmetry 9 (1998) 1.
A. Lee, W. Kim, J. Lee, T. Hyeon, B.M. Kim, Tetrahedron: Asymmetry 15 (2004) 2595.
A. Cwik, Z. Hell, A. Hegedüs, Z. Finta, Z. Horvath, Tetrahedron Lett. 43 (2002) 3985.
P. Zhou, J.E. Blubaum, C.T. Burns, N.R. Natale, Tetrahedron Lett. 38 (1997) 7019.
D.S. Clarke, R. Wood, Synth. Commun. 26 (1996) 1335.
G.K. Jnaneshwara, V.H. Deshpande, M. Lalithambika, T. Ravindranathan, A.V. Bedekar, Tetrahedron Lett. 39 (1998) 459.
I. Mohammadpoor-Baltork, A.R. Khosropour, S.F. Hojati, Synlett (2005) 2747.
N.N. Karade, G.B. Tiwari, S.V. Gampawar, Synlett (2007) 1921.
E.J. Corey, K. Ishihara, Tetrahedron Lett. 33 (1992) 6807.
S. Minakata, M. Nishimura, T. Takahashi, Y. Oderaotoshi, M. Komatsu, Tetrahedron Lett. 42 (2001) 9019.
K.S. Suslick, Ann. Rev. Mater, Sci. 29 (1999) 295.
M. Margulis, Sonochemistry and Cavitation, Gordon and Breach, New York, 1995.
R. Gedye, F. Smith, K. Westaway, H. Ali, L. Baldisera, L. Laberge, J. Rousell, Tetrahedron Lett. 27 (1986) 279.
S.A. Galema, Chem. Soc. Rev. 26 (1997) 233.
D.M.P. Mingos, A.G. Whittaker, in: R. van Eldik, C.D. Hubbard (Eds.), Microwave Dielectric Heating Effects in Chemical Synthesis, Chemistry Under Extreme or Non-Classical Conditions, Wiley, New York, 1997, p. 479–514.
H. Witte, W. Seeliger, Liebigs Ann. Chem. (1976) 996.
P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57 (2001) 9225.
A. de la Hoz, A. Diaz-Ortiz, A. Moreno, Chem. Soc. Rev. 34 (2005) 164.
C.O. Kappe, Angew. Chem. Int. Edit. 43 (2004) 6250.
I. Mohammadpoor-Baltork, A.R. Khosropour, S.F. Hojati, Cat. Commun. 8 (2007) 200.
G.K. Jnaneshwara, V.H. Deshpande, A.V. Bedekar, J. Chem. Res. (S) (1999) 252.
G. Desimoni, G. Faita, K.A. Jorgensen, Chem. Rev. 106 (2006) 3561.
T.J. Mason, J.-L. Luche, in: R.V. Eldick, C.D. Hubbard (Eds.), Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, 1997, p. 317.
K.S. Suslick, Ultrasound, Its Chemical, Physical and Biological Effect, VCH, Weinheim, 1988, p. 165.
J.F. Bower, C.J. Martin, D.J. Rawson, A.M.Z. Slawin, J.M.J. Williams, J. Chem. Soc., Perkin Trans. 1 (1996) 333.
H. Witte, W. Seeliger, Liebigs Ann. Chem. (1974) 996.
G.S. Poindexter, J. Heterocycl. Chem. 20 (1983) 1431.
L.N. Pridgen, J. Org. Chem. 47 (1982) 4319.
M.C. Pirrung, L.N. Tumey, J. Comb. Chem. 2 (2000) 675.
B. George, E.P. Papadopoulos, J. Org. Chem. 42 (1977) 441.
T. Kumagai, Y. Kawamura, T. Mukai, Tetrahedron Lett. 24 (1983) 2279.
B.P. Bandgar, S.S. Pandit, Tetrahedron Lett. 44 (2003) 2331.
A. Schöning, T. Debaerdemaeker, M. Zander, W. Friedrichsen, Chem. Ber. 122 (1989) 1119.
L. Chen, J. Mat. Sci. Lett. 22 (2003) 953.
Aldrich, Catalog Handbook of Fine Chemicals, 1988-1989, p. 1038.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Moghadam, M., Mirkhani, V., Tangestaninejad, S. et al. InCl3 as an efficient catalyst for synthesis of oxazolines under thermal, ultrasonic and microwave irradiations. JICS 6, 251–258 (2009). https://doi.org/10.1007/BF03245832
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03245832