Chem. 1996, 61, 8063-8068. (d) Ariffin, A.; Khan,
M. N.; Lan, L. C.; May, F. Y.; Yun, C. S. Syn.
Commun. 2004, 4439-4445. (e) Curley, O. M. S.;
McCormick, J. E.; McElhinney, R. S.; McMurry,
T. B. H. ARKIVOC 2003 (vii) 180-189.
The last phthalimide to be examined was the
N-(diethylphosphoryl)phthalimide 7. This
phthalimide was reacted with sec-butylamine,
benzylamine, and p-anisidine to afford the
corresponding N-alkyl and N-arylphthalimides.
The benzylamine reaction afforded the highest
yield (92%), p-anisidine led to an isolated yield of
62%, while the sec-butylamine led to a yield of
31%. In all cases, the byproduct (EtO)2PONH2
had to be removed by chromatography.
Ultimately, the phosphorylphthalimide proved to
be the most difficult to prepare and the least
effective in terms of product formation.
3. (a) S̀lusarska, E.; Zwierzak, A. Liebigs Ann. Chem.
1986, 1986, 402-405. (b) Sen, S. E.; Roach, S. L.
Synthesis 1995, 756-758. (c) Dandapani, S.
;Curran, D. P. Tetrahedron 2002, 58, 3855-3864.
4. Wuts, P. G. M.; Greene, T. W. Green’s
Protective Groups in Organic Synthesis, 4th
Edition 2007, Wiley and Sons, New York, Ch.
7, pp. 790-802. See also: (a) Sasaki, T.;
Minamoto, K.; Itoh, M. J. Org. Chem. 1978,
43, 2320. (b) Huynh, V.; Joyce, N.; Rieger, M.;
Walker, D.; Goldknopf, I.; Hill, T. S.; Jayaraman,
K.; Mulvey, D. Bioconjugate Chem. 1995, 6,
599-607. (c) Chandrasekhar, M. T.; Uma, G.
Tetrahedron Lett. 1997, 38, 8089. (d) Wang, Z.-
G.; Zhang, X.; Visser, D. L.; Zatorski, A.; Iserloh,
U.; Lloyd, K. O.; Danishefsky, S. J. Angew.
Chem., Int. Ed. 2001, 40, 1728. (e) Zhou, Z.;
Lin, Z.-X.; Liang, D.; Hu, J.-Q. Tetrahedron
2013, 69, 43-49.
5. Hoogwater, D. A.; Reinhoudt, D. N.; Lie, T. S.;
Gunneweg, J. J.; Beyerman, H. C. Recl. Trav.
Chem. Pays-Bas 1973, 92, 819.
6. Moore, J. A.; Kim, J.-H. Tetrahedron Lett. 1991,
32, 3449.
7. Casimir, J. R.; Guichard, G.; Briand, J.-P. J. Org.
Chem. 2002, 67, 3764.
8. Nguyen, T. B.; Sorres, J.; Tran, M. Q.; Ermolenko,
In summary, a series of phthalimides were
prepared in an effort to investigate the
development of variants of the Nefkens’ reagent.
The N-acetylphthalimide derivative 8a exhibited
unusual reactivity as compared to the other N-
acylated derivatives (8b-d).
(methanesulfonyl)phthalimide and the N-(diethyl
phosphoryl)phthalimide derivatives were
The N-
ultimately not as successful in the transamidation
process. The N-propanoylphthalimide (8b) was
determined to be the optimal reagent in this series
of phthalimides.
Acknowledgement
L.; Al-Mourabit, A. Org. Lett. 2012,
3202
9. Rao, S. N.; Mohan, D. C.; Adimurthy, S. Org. Lett.
2013, 15, 1496-1499.
14,
The authors acknowledge support from Illinois
State University.
10. (a) Nefkens, G. H. L.; Tesser, G. I.; Nivard, R. J. F.
Recl. Trav. Chem. Pays-Bas 1960, 79, 688. (b)
Nefkens, G. H. L. Nature 1960 185, 309. (c)
Nefkens, G. H. L.; Tesser, G. I. J. Am. Chem. Soc.
1961, 83, 1263. (d) Worster, P. M; Leznoff, C. C.;
McArthur, C. R. J. Org. Chem., 1980, 45, 174-175.
(e) McArthur, C. R.; Worster, P. M.; Okon, A.
U. Synth. Commun. 1983, 13, 311. (f) Sosnovsky,
G.; Lukszo, J. Naturforsch. B. 1986, 41B, 122. (g)
Bowen, E. G.; Wardrop, D. J. J. Am. Chem. Soc.,
2009, 131, 6062-6063. (h) Griesebeck, A. G.;
Neudörfl, J.; de Kiff, A. Beilstein J. Org. Chem.
2011, 7, 518.
Supplementary data
Supplementary data associated with this article
can be found, in the online version, at http:/
References and notes
1. (a) Gabriel, S. Chem. Ber. 1887, 20, 2224. (b)
Sheehan, J. C.; Bolhofer, V. A. J. Am. Chem. Soc.
1950, 72, 2786-2788. (c) Gibson, M. S.;
Bradshaw, R. W. Angew. Chem. Int. EEngl. 1968,
7, 919-930. (d) Le, Z.-G. ; Chen, Z.-C.; Hu, Y.;
Zheng, Q.-G. Synthesis, 2004, 208- 212.
11. Romero, C. M.; González, M. E. J. Chem. Eng.
Data, 2010, 55, 2326.
2. (a) Ing, H. R.; Manske, R. H. F. J. Chem. Soc.
1926, 2349-2351. (b) Khan, M. N. J. Org. Chem.
1995, 60, 4536-4541. (c) Khan, M. N. J. Org.
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