J. K. Augustine et al. / Tetrahedron Letters 52 (2011) 1074–1077
1077
12. Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2008, 73, 2894.
13. Ramalingan, C.; Park, Y. J. Org. Chem. 2007, 72, 4536.
14. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311.
work-up and can be used as a valid substitute for other methods,
thus avoiding the use of expensive and more toxic reagents to ac-
cess amides and nitriles from oximes.
15. De, S. K. Synth. Commun. 2004, 34, 3431.
16. De, S. K. J. Chem. Res. 2004, 131.
17. For a brief review of the reagent, see: (a) Llanes García, A. L. Synlett 2007, 1328;
(b) Schwarz, M. Synlett 2000, 1369.
Supplementary data
18. For other applications of T3P, see: (a) Burkhart, F.; Hoffmann, M.; Kessler, H.
Angew. Chem., Int. Ed. 1997, 36, 1191; (b) Wedel, M.; Walter, A.; Montforts, F.-P.
Eur. J. Org. Chem. 2001, 1681; (c) Hermann, S. Ger. Offen. DE 10063493, 2002;
Chem. Abstr. 2002, 137, 47003.; (d) Meudt, A.; Scherer, S.; Nerdinger, S. PCT Int.
Appl. WO 2005070879, 2005; Chem. Abstr. 2005, 143, 172649.; (e) Meudt, A.;
Scherer, S.; Böhm, C. PCT Int. Appl. WO 2005102978, 2005; Chem. Abstr. 2005,
143, 440908.; (f) Zumpe, F. L.; Melanie, F.; Schmitz, K.; Lender, A. Tetrahedron
Lett. 2007, 48, 1421; (g) Augustine, J. K.; Atta, R. N.; Ramappa, B. K.; Boodappa,
C. Synlett 2009, 3378; (h) Augustine, J. K.; Vairaperumal, V.; Narasimhan, S.;
Alagarsamy, P.; Radhakrishnan, A. Tetrahedron 2009, 65, 9989; (i) James, M.;
Crawforth, J. M.; Paoletti, M. Tetrahedron Lett. 2009, 50, 4916; (j) Vasantha, B.;
Hemantha, H. P.; Sureshbabu, V. V. Synthesis 2010, 2990.
Supplementary data (characterization data for new compounds,
copies of 1H and 13C NMR spectra for 1a–v, 2a–v, 3a–n, 4a–n, and
LCMS report for 2a–v, and 4a–n) associated with this article can be
References and notes
1. (a) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; John Wiley &
Sons: New York, 2001. p 1415; (b) Gawley, R. E. Org. React. 1988, 35, 1.
2. Luedeke, V. D. In Encyclopedia of Chemical Processing and Design; Mcketta, J. J.,
Ed.; Marcel Dekker: New York, 1978; p 72.
3. (a) Dongare, M. K.; Bhagwat, V. V.; Ramana, C. V.; Gurjar, M. K. Tetrahedron Lett.
2004, 45, 4759; (b) Ghiaci, M.; Abbaspur, A.; Kalbasi, R. Appl. Catal., A 2005, 287,
83; (c) Forni, L.; Fornasari, G.; Giordano, G.; Lucarelli, C.; Katovic, A.; Trifiro, F.;
Perri, C.; Nagy, J. B. Phys. Chem. Chem. Phys. 2004, 6, 1842.
4. (a) Furuya, Y.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 11240; (b)
De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272; (c)
Kusama, H.; Yamashita, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 373; (d)
Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Tetrahedron Lett. 2004, 45,
3369; (e) Li, D.; Shi, F.; Guo, S.; Deng, Y. Tetrahedron Lett. 2005, 46, 671; (f)
Chandrasekhar, S.; Gopalaiah, K. Tetrahedron Lett. 2002, 43, 2455.
5. (a) Boero, M.; Ikeshoji, T.; Liew, C. C.; Terakura, K.; Parrinello, M. J. Am. Chem.
Soc. 2004, 126, 6280; (b) Ikushima, Y.; Hatakeda, K.; Sato, M.; Sato, O.; Arai, M.
Chem. Commun. 2002, 19, 2208; (c) Ikushima, Y.; Hatakeda, K.; Sato, O.;
Yokoyama, T.; Arai, M. Angew. Chem., Int. Ed. 1999, 38, 2910.
19. All of the oxime substrates used in this investigation were synthesized in
quantitative yields by refluxing a mixture of 1 equiv of the corresponding
ketones or aldehydes, 1.6 equiv of hydroxylamine hydrochloride, and 2.0 equiv
of sodium acetate in aqueous methanol.
20. T3P catalyzed synthesis of amides/lactams from ketoximes: To a solution of
ketoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol %, 50% soln in
EtOAc) and the resulting reaction mixture was stirred at reflux for 1–4 h under
nitrogen atmosphere. When the reaction was completed as confirmed by TLC,
the solvent was removed under vacuum and the residue was diluted with
water (20 mL). The product was extracted with ethyl acetate (2 Â 20 mL) and
the combined organic phase was washed with saturated NaHCO3 solution
(1 Â 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4.
The solvent was removed under reduced pressure to afford the desired amides
in good purity.
21. T3P catalyzed synthesis of nitriles from aldoximes: To a solution of aldoxime
(0.01 mol) in THF (10 mL) was added T3P (15 mol %, 50% soln in EtOAc) and the
resulting reaction mixture was stirred at room temperature for 1–2 h under
nitrogen atmosphere. When the reaction was completed as confirmed by TLC,
the solvent was removed under vacuum and the residue was diluted with
water (20 mL). The product was extracted with ethyl acetate (2 Â 20 mL) and
the combined organic phase was washed with saturated NaHCO3 solution
(1 Â 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4.
The solvent was removed under reduced pressure to afford the desired nitriles
in good purity.
6. (a) Guo, S.; Du, Z.; Zhang, S.; Li, D.; Li, Z.; Deng, Y. Green Chem. 2006, 8, 296; (b)
Guo, S.; Deng, Y. Catal. Commun. 2005, 6, 225.
7. Chandrasekhar, S.; Gopalaiah, K. Tetrahedron Lett. 2003, 44, 755.
8. Chandrasekhar, S.; Gopalaiah, K. Tetrahedron Lett. 2003, 44, 7437.
9. Zhu, M.; Cha, C.; Deng, W.; Shi, X. Tetrahedron Lett. 2006, 47, 4861.
10. Sardarian, A. R.; Shahsavari-Fard, Z.; Shahsavari, H. R.; Ebrahimi, Z. Tetrahedron
Lett. 2007, 48, 2639.
11. Xiao, L.; Xia, C.; Chen, J. Tetrahedron Lett. 2007, 48, 7218.